Differentiation of Diastereoisomers of Protected 1,2-Diaminoalkylphosphonic Acids by EI Mass Spectrometry and Density Functional Theory
|
|
- Ἀκελδαμά Καζαντζής
- 6 χρόνια πριν
- Προβολές:
Transcript
1 SUPPLEMENTARY MATERIALS Differentiation of Diastereoisomers of Protected 1,2-Diaminoalkylphosphonic Acids by EI Mass Spectrometry and Density Functional Theory Ewelina Drabik, 1 Grzegorz Krasiński, 2 Marek Cypryk, 2 Roman Błaszczyk, 3 Tadeusz Gajda, 3 Marek Sochacki 1 1 Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Laboratory for Analysis of Organic Compounds and Polymers, Sienkiewicza 112, Łódź, Poland 2 Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Computer Modeling, Sienkiewicza 112, Łódź, Poland 3 Lodz University of Technology, Institute of Organic Chemistry, Żeromskiego 116, Łódź, Poland Table of contents The procedure for synthesis of compounds 7_a and 8_a...2 Diethyl dideuteriohydroxymethylphosphonate [1] (1)...2 Diethyl azidodideuteriomethylphosphonate [2] (2)...3 Diethyl dideuterioisothiocyanatomethylphosphonate [3] (3)...4 Diethyl trans- and cis-(4-deuterio-5-phenyl-2-thioxoimidazolidin-4-yl)phosphonates [4] (cis- 7_a and trans-8_a)...4 References...5 Mass spectra...6 Theoretical calculations...8 1
2 The procedure for synthesis of compounds 7_a and 8_a Diethyl dideuteriohydroxymethylphosphonate [1] (1), diethyl azidodideuteriomethylphosphonate [2] (2), diethyl dideuterioisothiocyanatomethylphosphonate [3] (3), diethyl trans- and cis-(4-deuterio-5- phenyl-2-thioxoimidazolidin-4-yl)phosphonates [4] (4) were prepared according to the procedures described in the literature. N-tert-Butyl-benzylidenecarbamate [5] (N-Boc-imine) was prepared as described previously. Diastereoisomeric mixture of compound 7_a and 8_a was resolved into individual cis- and trans-diastereoisomers using preparative TLC (Analtech UV254 plates were used). The homogeneity of the samples was confirmed by TLC analysis and 31 P and 1 H NMR spectroscopy. Scheme S1. Synthesis of diethyl trans- and cis-(4-deuterio-5-phenyl-2-thioxoimidazolidin-4- yl)phosphonates (7_a and 8_a). Diethyl dideuteriohydroxymethylphosphonate [1] (1) A mixture of paraformaldehyde-d 2 (1.0 g, 31.2 mmol), diethyl phosphonate (3.9 g, 28.3 mmol) and triethylamine (1.44 g, 14.2 mmol) was slowly heated to 60 o C for 30 minutes. Next, the suspension was heated for 1.5 h at o C until all paraformaldehyde was dissolved. Excess of triethylamine was evaporated under reduced pressure, and the oily residue was subjected to bulb 2
3 to bulb distillation ( o C/0.3 Torr) to give pure diethyl dideuteriohydroxymethylphosphonate (1) (2.88 g, 59.8%) as a pale yellow oil. 31 P NMR (101 MHz, CDCl 3, δ): H NMR (250 MHz, CDCl 3, δ): 1.33 (brt, 3 J HH 7.1 Hz, 6H, 2CH 3 CH 2 O), (m, 4H, 2CH 3 CH 2 O), 4.35 (brs, 1H, OH) 13 C NMR (63 MHz, CDCl 3, δ): 14.5 (d, 3 J CP 5.6 Hz, 2CH 3 CH 2 O), X (dqu, 1 J CP Hz, 1 J CD Hz, CD 2 ), 60.6 (d, 2 J CP 6.8 Hz, 2CH 3 CH 2 O) IR (ATR, ν): 3311, 2908, 1229, 1017, 967 HRMS (EI, 70 ev): m/z calcd for C 5 H 11 D 1 P 1 O 4 : ; found: Diethyl azidodideuteriomethylphosphonate [2] (2) A solution of DEAD (1.89 g, 10.8 mmol) in anhydrous CH 2 Cl 2 (3 ml) was added dropwise with stirring and external cooling (dry ice/acetone bath) to a solution of Ph 3 P (2.84 g, 10.8 mmol) in CH 2 Cl 2 (25 ml) at 5 o C. The mixture was cooled to 10 o C and 1.0 M solution of HN 3 in toluene (11.25 ml, mmol) was added dropwise at this temperature. The solution of diethyl dideuteriohydroxymethylphosphonate (1) (8.0 mmol) was then added and stirring was continued for 24 hours at room temperature. The mixture was cooled to 0 o C, partialy precipitated ethyl 3- (ethoxycarbonyl)carbazate was filtered off, the filtrate was evaporated under reduced pressure, and the semi-solid residue was extracted with hexane (4 50 ml). The combined extracts were evaporated under reduced pressure to give crude azide 2. The oily residue was next subjected to bulb to bulb distillation (75 90 o C/0.2 Torr) to give pure diethyl azidodideuteriomethylphosphonate (2) (1.4 g, 89.7%) as a pale yellow oil. Warning: Since hydrazoic acid (HN 3 ) is highly toxic azidation reaction should be carried out under the well ventilated hood and behind the protective screen. 31 P NMR (101 MHz, CDCl 3, δ): H NMR (250 MHz, CDCl 3, δ): 1.33 (brt, 3 J HH 7.1 Hz, 6H, 2CH 3 CH 2 O), 4.20 (dq, 3 J HH 7.1 Hz, 3 J HP 8.2 Hz, 4H, 2CH 3 CH 2 O) 13 C NMR (63 MHz, CDCl 3, δ): 14.6 (d, 3 J CP 5.7 Hz, 2CH 3 CH 2 O), X (dqu, 1 J CP Hz, 1 J CD Hz, CD 2 ), 61.1 (d, 2 J CP 6.6 Hz, 2CH 3 CH 2 O), IR (ATR, ν): 2921, 2124, 2095, 1241, 1018, 968 HRMS (EI, 70 ev): m/z calcd for C 5 H 10 D 2 P 1 N 3 O 3 : ; found:
4 Diethyl dideuterioisothiocyanatomethylphosphonate [3] (3) Ph 3 P (1.76 g, 6.71 mmol, 1.05 equiv) was added in one portion with stirring and external cooling (ice bath) to a solution of diethyl azidodideuteriomethylphosphonate (2) (1.25 g, 6.41 mmol) in anhydrous toluene (20 ml). Stirring was continued for 3 h at room temperature, and CS 2 (3.91 g, 3.1 ml, 51.0 mmol) was then added in one portion. Next, the mixture was kept at room temperature for 2 days. Toluene and excess of CS 2 was evaporated under reduced pressure, and the semi-crystalline residue was extracted with hexane (4 40 ml) to remove most of Ph 3 PS. The combined extracts were evaporated under reduced pressure, and the oily residue was subjected to bulb to bulb distillation ( o C / Torr) to give pure diethyl dideuterioisothiocyanatomethylphosphonate (3) (0.95 g, 70.2%) as a colorless oil [R f (AcOEt/Hexanes 3:1 v/v) 0.45]. 31 P NMR (101 MHz, CDCl 3, δ): H NMR (250 MHz, CDCl 3, δ): 1.38 (brt, 3 J HH 7.1 Hz, 6H, 2CH 3 CH 2 O), (m, 4H, 2CH 3 CH 2 O) 13 C NMR (63 MHz, CDCl 3, δ): 16.3 (d, 3 J CP 5.7 Hz, 2CH 3 CH 2 O), 39.8 (dqu, 1 J CP Hz, 1 J CD 21.8 Hz, CD 2 ), 61.1 (d, 2 J CP 6.6 Hz, 2CH 3 CH 2 O), (brs, NCS). IR (ATR, ν): 2982, 2074, 1253, 1052,1012, 971 HRMS (EI, 70 ev): m/z calcd for C 6 H 10 D 2 P 1 N 1 O 3 S 1 : ; found: Diethyl trans- and cis-(4-deuterio-5-phenyl-2-thioxoimidazolidin-4-yl)phosphonates [4] (cis- 7_a and trans-8_a) A solution of NaHMDS (0.5 M, 0.6 ml, 1.2 mmol) in THF (15 ml) was cooled to 75 o C. Next a solution of diethyl dideuterioisothiocyanatomethylphosphonate (3) (0.211 g, 1.0 mmol) and N- tert-butyl-benzylidenecarbamate (N-Boc-imine) (0.205 g, 1.0 mmol) in THF (3 ml) was added dropwise to the reaction mixture. The mixture was stirred for 3 h at 75 o C and then quenched with D 2 O (1.5 ml). The mixture was stirred for 30 min at 0 o C. A saturated aq solution of NH 4 Cl (3 ml) was added and the mixture was diluted with methylene chloride (60 ml). Organic layer was separated and was washed successively with saturated aq NH 4 Cl (2 ml), water (2 ml), then dried (MgSO 4 ) and concentrated under reduced pressure to give g (88.8%) of crude imidazolidine-2-thiones 4. Analytically pure trans- and cis-isomers of 4 were isolated after preparative TLC (AcOEt/hexanes 5:1 v/v). 4
5 cis-7_a. Yield: 63 mg (15%), colorless solid, mp o C; R f (AcOEt/hexanes 5:1 v/v) P NMR (101 MHz, CDCl 3, δ): H NMR (250 MHz, CDCl 3, δ): 1.03 (t, 3 J HH 7.1 Hz, 3H, CH 3 CH 2 O), (m, 12H, C(CH 3 ) 3 + CH 3 CH 2 O), (m, 1H, CH 3 CH 2 O), (m, 1H, CH 3 CH 2 O), (m, 2H, CH 3 CH 2 O), 6.83 (brs, 1H, NH), (m, 5H ar ); 13 C NMR (63 MHz, CDCl 3, δ): 16.2, 16.3 (2d, 3 J CP 5.8 Hz, 2CH 3 CH 2 O), 27.6 (s, C(CH 3 ) 3 ), 55.0 (dt, 3 J CP Hz, 3 J CD 21.0 Hz, CDP), 62.8(d, 2 J CP 6.4 Hz, 2CH 3 CH 2 O), 64.2 (s, CHP), 83.7 (s, C(CH 3 ) 3 ), 128.3, (CH ar ), (d, 3 J CP 6.0 Hz, CHC ar ), (s, C=O), (d, 3 J CP 9.8 Hz,, C=S). IR (ATR, ν): 3164, 2977, 1744, 11496, 1250, 1139, 1012, 960. HRMS (EI, 70 ev): m/z calcd for C 18 H 26 D 1 P 1 N 2 O 6 S 1 : ; found: trans-8_a. Yield: 108 mg (26%), colorless viscous oil; R f (AcOEt/hexanes 5:1 v/v) P NMR (101 MHz, CDCl 3, δ): H NMR (250 MHz, CDCl 3, δ): 1.28 (s, 9H, C(CH 3 ) 3 ), 1.35, 1.36 (2t, 3 J HH 7.1 Hz, 6H, 2CH 3 CH 2 O), (m, 4H, 2CH 3 CH 2 O), 5.54 (d, 3 J HP 19.6 Hz, 1H, CHCHP), (m, 5H ar ), 7.75 (brs, 1H, NH). 13 C NMR (63 MHz, CDCl 3, δ): 16.5, 16.6 (2d, 3 J CP 5.4 Hz, 2CH 3 CH 2 O), 27.7 (s, C(CH 3 ) 3 ), 57.5 (dt, 3 J CP Hz, 1 J CD 21.0 Hz CDP), 63.6 (d, 2 J CP 7.0 Hz, CH 3 CH 2 O), 63.9 (s, CHPh), 64.3 (d, 2 J CP 76.3 Hz, CH 3 CH 2 O), 83.6 (s, C(CH 3 ) 3 ), 125.3, 128.6, (CH ar ), (d, 3 J CP 12.6 Hz, CHC ar ), (brs, C=O), (brs, C=S). IR (ATR, ν): 3158, 2979, 1751, 1711, 1492, 1227, 1134, 1012, 972. HRMS (EI, 70 ev): m/z calcd for C 18 H 26 D 1 P 1 N 2 O 5 S 1 : ; found: References 1. Baraldi, P.G., Guarneri, M., Moroder, F., Pollini, G.P., Simoni, D.: Synthesis of 1- Phthalimidoalkanephosphonates. Synthesis (1982) 2. Gajda, T., Matusiak, M.: An Expedient Synthesis of Diethyl 1-Azidoalkylphosphonates via the Mitsunobu Reaction. Synthesis (1992). 3. Sikora, D., Gajda, T.: A Facile Synthesis of Diethyl 1-(Isothiocyano)alkylphosphonates. Phosphorus, Sulfur and Silicon 157, (2000). 4. Błaszczyk, R., Gajda, T.: Direct synthesis of protected diethyl 1,2- diaminoalkylphosphonates. Tetrahedron Lett. 48, (2007) 5. Cowen, B.J., Saunders, L.B., Miller, S.J.: Pyridylalanine (Pal)-Peptide Catalyzed Enantioselective Allenoate Additions to N-Acyl Imines. J. Am. Chem. Soc. 131, (2009) 5
6 Mass spectra Figure S1. EI mass spectra of a) cis-1, b) trans-2, c) cis-3, d) trans-4, e) cis-5, f) trans-6, g) cis-7 and h) trans-8. 6
7 Figure S2. Product ion mass spectra of molecular ion of compounds a) cis-1, b) trans-2, c) cis-3 and d) trans-4. 7
8 Theoretical calculations To confirm the stability of each diastereoisomer the conformer analysis of molecular ion of cis-1 and trans-2 was performed. SUB_cis_1 SUB_cis_1 SUB_cis_1 SUB_cis_1 Figure S3. Different conformations of molecular ion of cis-1 (SUB_cis) isomer. 8
9 SUB_trans_2 SUB_trans_2 SUB_trans_2 SUB_trans_2 Figure S4. Different conformations of molecular ion of trans-2 (SUB_trans) isomer. 9
10 Table S1. Comparison of the B3LYP and M06-2x functionals. cis trans structure B3LYP/ M06-2x/ G(2d,p) G(2d,p) SUB_cis_ TS1_E_H c _ INT_E_H c _ TS2_E_H c _ IC_E_H c _ SUB_trans_ TS1_E_H c _ INT_E_H c _ TS2_E_H c _ IC_E_H c _ Table S2. Thermodynamic properties of the cis-1 and trans-2 conformers. As a reference for the G relative (B3LYP/6-311+G(2d,p)//B3LYP/6-31G*) the G of most stable conformer was used. E electron 1 G absolut 1 G relative 2 SUB_cis_ SUB_cis_ SUB_cis_ SUB_cis_ SUB_trans_ SUB_trans_ SUB_trans_ SUB_trans_ Ha 2 kcal/mol Table S3. Electron spin density of SUB_cis_1 and SUB_trans_1 structures. SUB_cis_1 SUB_trans_1 Mulliken NPA Mulliken NPA N C N C C S P O O O
11 Table S4. Comparison of the optimized bond lengths [Å] between the ground state and cationic radical form for cis-1 and trans-2. cis-1 trans-2 Bond Neutral Free radical Difference Neutral Free radical Difference C 2 -S N 3 -C N 1 -C C 4 -N C 5 -N C 4 -C C 4 -P Table S5. NPA spin densities for main atoms in function of reaction coordinate for loss of the diethoxyphosphoryl radical, phenyl ring, H c and H d. a) cis isomer substrate transition states SUB_cis-1 TS_L_PO_1 TS_L_Ph_1 TS_L_H c _1 TS_L_H d _1 N C N C C S P O O O H a H b H c H d C Ph
12 b) trans isomer substrate transition states SUB_trans-2 TS_L_PO_2 TS_L_Ph_2 TS_L_H c _2 TS_L_H d _2 N C N C C S P O O O H a H b H c H d C Ph Table S6. NPA spin densities for main atoms in function of reaction coordinate for elimination of DEPI for exemplary reaction pathways (a) and (c). a) pathway (a) for cis isomer SUB_cis-1 TS1_E_H a _1 INT_E_H a _1 TS2_E_H a _1 IC_E_H a _1 N C N C C S P O O O H a H b H c H d C Ph
13 b) pathway (a) for trans isomer SUB_trans-2 TS1_E_H a _2 INT_E_H a _2 TS2_E_H a _2 IC_E_H a _2 N C N C C S P O O O H a H b H c H d C Ph c) pathway (c) for cis isomer SUB_cis-1 TS1_E_H c _1 INT_E_H c _1 TS2_E_H c _1 IC_E_H c _1 N C N C C S P O O O H a H b H c H d C Ph
14 d) pathway (c) for trans isomer SUB_trans-2 TS1_E_H c _2 INT_E_H c _2 TS2_E_H c _2 IC_E_H c _2 N C N C C S P O O O H a H b H c H d C Ph
15 Table S7. NPA spin densities for intermediates INT. (most significant are in bold) cis-1 trans-2 INT_E_H a INT_E_H b INT_E_H c INT_E_H d INT_E_H e INT_E_H a INT_E_H b INT_E_H c INT_E_H d INT_E_H e N C N C C S P O O O C_Ph C_orto C_orto C_meta C_meta C_para Full reference 12: Frisch, M J, Trucks, G. W., Schlegel, H. B., Robb, M. A., Cheeseman, J. R., Montgomery, J. A. Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomeli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, 15
16 S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. Gaussian 03, Revision C.02. Gaussian, Inc. Wallingford CT 16
Bifunctional Water Activation for Catalytic Hydration of Organonitriles
Supporting Information (16 pages including the cover page) Bifunctional Water Activation for Catalytic Hydration of Organonitriles Prosenjit Daw, Arup Sinha, S. M. Wahidur Rahaman, Shrabani Dinda and Jitendra
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Supporting information Chiral Thiourea-Based Bifunctional Organocatalysts in the Asymmetric Nitro- Michael Addition:
Διαβάστε περισσότεραSupporting Information. A single probe to sense Al(III) colorimetrically and. Cd(II) by turn-on fluorescence in physiological
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Supporting Information A single probe to sense Al(III) colorimetrically and Cd(II) by
Διαβάστε περισσότεραSupporting Information. Identification of Absolute Helical Structures of Aromatic Multi-layered Oligo(m-phenylurea)s in Solution.
Supporting Information Identification of Absolute Helical Structures of Aromatic Multi-layered Oligo(m-phenylurea)s in Solution. Mayumi Kudo, 1 Takayuki Hanashima, 2 Atsuya Muranaka, 3,* Hisako Sato, 4,5,
Διαβάστε περισσότεραStriking Difference between Succinimidomethyl and Phthalimidomethyl Radicals in Conjugate Addition to Alkylidenemalonate Initiated by Dimethylzinc
Striking Difference between Succinimidomethyl and Phthalimidomethyl Radicals in Conjugate Addition to Alkylidenemalonate Initiated by Dimethylzinc Ken-ichi Yamada*, Yusuke Matsumoto, Shintaro Fujii, Takehito
Διαβάστε περισσότεραDiels-Alder reaction of acenes with singlet and triplet oxygen - theoretical study of two-state reactivity
Supporting Information Diels-Alder reaction of acenes with singlet and triplet oxygen - theoretical study of two-state reactivity A. Ravikumar Reddy and Michael Bendikov* Computational details: Density
Διαβάστε περισσότεραStructural Expression of Exo-Anomeric Effect
Supporting Information for Structural Expression of Exo-Anomeric Effect Elena R. Alonso, Isabel Peña, Carlos Cabezas, and José L. Alonso* Contents Table S1: Transition frequencies of conformer cc-β- 4
Διαβάστε περισσότεραReaction of Lithium Diethylamide with an Alkyl Bromide and Alkyl Benzenesulfonate: Origins of Alkylation, Elimination, and Sulfonation.
Reaction of Lithium Diethylamide with an Alkyl omide and Alkyl Benzenesulfonate: rigins of Alkylation, Elimination, and ulfonation. Lekha Gupta, Antonio Ramírez and David B. Collum* Contribution from the
Διαβάστε περισσότεραA Selective, Sensitive, Colorimetric and Fluorescence Probe. for Relay Recognition of Fluoride and Cu (II) ions with
Supporting Information for A Selective, Sensitive, Colorimetric and Fluorescence Probe for Relay Recognition of Fluoride and Cu (II) ions with OFF-ON-OFF Switching in Ethanol-Water Solution Yu Peng,* Yu-Man
Διαβάστε περισσότεραNesting Complexation of C 60 with Large, Rigid D 2 Symmetrical Macrocycles
Supporting Information for: Nesting Complexation of C 60 with Large, Rigid D 2 Symmetrical Macrocycles Marco Caricato, a Carmine Coluccini, a Daniele Dondi, b Douglas Vander Griend, c and Dario Pasini,
Διαβάστε περισσότεραSupporting Information. DFT Study of Pd(0)-Promoted Intermolecular C H Amination with. O-Benzoyl Hydroxylamines. List of Contents
Supporting Information DFT Study of Pd(0)-Promoted Intermolecular C H Amination with O-Benzoyl Hydroxylamines Yunfei Zhou and Xiaoguang Bao* College of Chemistry, Chemical Engineering and Materials Science,
Διαβάστε περισσότεραPhotostimulated Reduction of Nitriles by SmI 2. Supporting information
Photostimulated Reduction of Nitriles by SmI 2 Chintada Nageswara Rao and Shmaryahu Hoz * Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel E-mail: shoz@mail.biu.ac.il Supporting information
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VC 2009 69451 Weinheim, Germany S1 Supporting Information for: The Lowest Singlet and Triplet States of the Oxyallyl Diradical Takatoshi Ichino, Stephanie M. Villano, Adam
Διαβάστε περισσότεραFigure S12. Kinetic plots for the C(2)-H/D exchange reaction of 2 CB[7] as a function
Supporting Information Encapsulation of Vitamin B 1 and its Phosphate Derivatives by Cucurbit[7]uril: Tunability of the Binding Site and Affinity by the Presence of Phosphate Groups Shengke Li, Hang Yin,
Διαβάστε περισσότεραCapture of Benzotriazole-Based Mannich Electrophiles by CH-Acidic Compounds
Capture of Benzotriazole-Based Mannich Electrophiles by CH-Acidic Compounds Jean-Christophe M. Monbaliu, a,b Lucas K. Beagle, a Finn K. Hansen, a,c Christian V. Stevens, b Ciaran McArdle d and Alan R.
Διαβάστε περισσότεραSynthesis, characterization and luminescence studies of
Supporting Information for Synthesis, characterization and luminescence studies of gold(i) HC amide complexes Adrián Gómez-Suárez, David J. elson, David G. Thompson, David B. Cordes, Duncan Graham, Alexandra
Διαβάστε περισσότεραAccessory Publication
Accessory Publication Pitfalls in the Photoelectron Spectroscopic Investigations of Benzyne. Photoelectron Spectrum of Cyclopentadienylideneketene. Anna Chrostowska, A,C Genevieve Pfister-Guillouzo, A
Διαβάστε περισσότεραA facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Διαβάστε περισσότεραSupporting Information
Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and
Διαβάστε περισσότεραCopper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information to the paper Theoretical Insights into the Separation
Διαβάστε περισσότεραSupporting Information. Lithium Cadmate-Mediated Deprotonative Metalation of Anisole: Experimental and Computational Study
Supporting Information Lithium Cadmate-Mediated Deprotonative Metalation of Anisole: Experimental and Computational Study Katia Snégaroff, Shinsuke Komagawa, Mitsuhiro Yonehara, Floris Chevallier, Philippe
Διαβάστε περισσότεραElectronic Supplementary Information for
Electronic Supplementary Information for Paper Title: Molecular mechanism of acid-triggered aryl-halide crosscoupling reaction via reductive elimination in well-defined aryl-cu III -halide species Authors:
Διαβάστε περισσότεραSite-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran
1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
Διαβάστε περισσότεραTitle N-H versus C-H Activation of a Pyrrole Imine at {Cp*Ir}: A Computational and Experimental Study
Supporting Information for: Title N-H versus C-H Activation of a Pyrrole Imine at {Cp*Ir}: A Computational and Experimental Study David L. Davies,* a Steven M. A. Donald, b Omar Al-Duaij, a John Fawcett,
Διαβάστε περισσότεραEthyl Nitroacetate in Aza-Henry Addition on Trifluoromethyl Aldimines: A Solvent-Free Procedure To Obtain Chiral Trifluoromethyl α,β-diamino Esters
Supporting Information Ethyl Nitroacetate in Aza-Henry Addition on Trifluoromethyl Aldimines: A Solvent-Free Procedure To Obtain Chiral Trifluoromethyl α,β-diamino Esters Luca Parise, Alessia Pelagalli,
Διαβάστε περισσότεραSupporting Information for
Supporting Information for Hydrogen-Bridged Digermyl and Germylsilyl Cations N. Kordts, C. Borner, R. Panisch, W. Saak, T. Müller* Contents. 1. Computational Details 2. IR Spectroscopic Results 3. NMR-Spectroscopic
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Hydrolysis of cis- and transplatin: structure and reactivity
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2008 Organocatalytic Asymmetric Hydrophosphination of α,β- Unsaturated Aldehydes: Development, Mechanism and DFT Calculations
Διαβάστε περισσότεραAlkyl-functionalization of 3,5-bis(2-pyridyl)-1,2,4,6- thiatriazine
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Electronic Supporting Information
Διαβάστε περισσότεραElectronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2013
General. All manipulations were carried out under an inert atmosphere of dry nitrogen using standard Schlenk techniques or in an inert-atmosphere glove-box. Solvents were dried form the appropriate drying
Διαβάστε περισσότεραSupplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
Διαβάστε περισσότεραSupporting Information
Supporting Information Imidazol(in)ium Hydrogen Carbonates as a Genuine Source of N- Heterocyclic Carbenes (NHCs): Applications to the Facile Preparation of NHC Metal Complexes and to NHC- Organocatalyzed
Διαβάστε περισσότεραElectronic Supplementary Information (ESI) for
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information (ESI) for A Kinetically Blocked 1,14:11,12- Dibenzopentacene:
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Luminescent Organoboron Ladder Compounds via Directed Electrophilic
Διαβάστε περισσότεραDFT Kinetic Study of the Pyrolysis Mechanism of Toluene Used for Carbon Matrix
2001 59 1, 17 21 ACTA CHIMICA SINICA Vol 59, 2001 No 1, 17 21 a,d Ξ a b b a a ( a b 710069) c d ( c 100083) ( d 710072) UB3LYP/ 3-21G 3 5 298 1 223 K : 963 K, 0 = 402 27 kj/ mol ; 963 K 1 223 K, E 0 =
Διαβάστε περισσότεραSupporting Information
Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State
Διαβάστε περισσότεραDivergent synthesis of various iminocyclitols from D-ribose
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,
Διαβάστε περισσότεραEnantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,
Διαβάστε περισσότεραSupplementary information
Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles
Διαβάστε περισσότεραRoom Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled
Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal
Διαβάστε περισσότεραRhodium-Catalyzed Direct Bis-cyanation of. Arylimidazo[1,2-α]pyridine via Double C-H Activation
Supporting Information Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation Xinju Zhu, Xiao-Jing Shen, Zi-Yao Tian, Shuai Lu, Lu-Lu Tian, Wen-Bo Liu, Bing Song,*
Διαβάστε περισσότεραSupporting Information
Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General
Διαβάστε περισσότεραMild Aliphatic and Benzylic hydrocarbon C H Bond Chlorination Using Trichloroisocyanuric Acid (TCCA)
Mild Aliphatic and Benzylic hydrocarbon C H Bond Chlorination Using Trichloroisocyanuric Acid (TCCA) Sascha H. Combe, Abolfazl Hosseini, Alejandro Parra, # and Peter R. Schreiner*, Institute of Organic
Διαβάστε περισσότεραPush-Pull Type Porphyrin Based Sensitizers: The Effect of Donor Structure on the Light- Harvesting Ability and Photovoltaic Performance
Push-Pull Type Porphyrin Based Sensitizers: The Effect of Donor Structure on the Light- Harvesting Ability and Photovoltaic Performance Item Type Article Authors Qi, Qingbiao; Li, Renzhi; Luo, Jie; Zheng,
Διαβάστε περισσότεραHiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Philippe Pierrat, Philippe Gros* and Yves Fort Synthèse Organométallique
Διαβάστε περισσότεραFirst DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of
Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch
Διαβάστε περισσότεραand Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu
Διαβάστε περισσότεραSupporting Information. Generation of Pyridyl Coordinated Organosilicon Cation Pool by Oxidative Si-Si Bond Dissociation
Supporting Information Generation of Pyridyl Coordinated Organosilicon Cation Pool by Oxidative Si-Si Bond Dissociation Toshiki okami, Ryoji Soma, Yoshimasa Yamamoto, Toshiyuki Kamei, Kenichiro Itami,
Διαβάστε περισσότεραIntermolecular Aminocarbonylation of Alkenes using Cycloadditions of Imino-Isocyanates. Supporting Information
Intermolecular Aminocarbonylation of Alkenes using Cycloadditions of Imino-Isocyanates Amanda Bongers, Christian Clavette, Wei Gan, Serge I. Gorelsky, Lyanne Betit, Kaitlyn Lavergne, Thomas Markiewicz,
Διαβάστε περισσότεραChemical Communications. Electronic Supporting Information
Chemical Communications Electronic Supporting Information Access to unusual polycyclic spiro enones from 2,2 -bis(allyloxy)-1,1 -binaphthyls using Grubbs catalysts: An unprecedented one-pot RCM/Claisen
Διαβάστε περισσότεραSyntheses and Characterizations of Molecular Hexagons and Rhomboids and Subsequent Encapsulation of Keggin-Type Polyoxometalates by Molecular Hexagons
Supporting Information for Syntheses and Characterizations of Molecular Hexagons and Rhomboids and Subsequent Encapsulation of Keggin-Type Polyoxometalates by Molecular Hexagons Kazuhiro Uehara, Takamichi
Διαβάστε περισσότεραZn 2 +, Studies on the Structures and Antihyperglycemic Effects of Zn 2 +, Cu 2 +, Ni 2 + 2Metformin Complexes. ZHU, Miao2Li LU, Li2Ping YANG, Pin Ξ
2004 62 8, 783 788 ACTA CHIMICA SINICA Vol 62, 2004 No 8, 783 788 Zn 2 +, Cu 2 + Ni 2 + Ξ Ξ ( 030006) Zn 2 +, Cu 2 +, Ni 2 + :Zn 2 +, Cu 2 +, Ni 2 +, N, N, N, N,, Studies on the Structures and Antihyperglycemic
Διαβάστε περισσότεραFacile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*
Facile construction of the functionalized 4H-chromene via tandem benzylation and cyclization Jinmin Fan and Zhiyong Wang* Hefei National Laboratory for Physical Science at Microscale, Joint- Lab of Green
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Supporting Information A Possible
Διαβάστε περισσότεραSupporting Information
Supporting Information Tris(pyrazolyl)methanides of the Alkaline Earth Metals - Influence of the Substitution Pattern on Stability and Degradation Christoph Müller, Alexander Koch, Helmar Görls, Sven Krieck,
Διαβάστε περισσότεραSupporting Information
Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei
Διαβάστε περισσότεραNovel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory
Διαβάστε περισσότεραSupporting Information
Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla
Διαβάστε περισσότεραSupporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Διαβάστε περισσότεραSequential Addition of Phosphine to Alkynes for the Selective. Synthesis of 1,2-Diphosphinoethanes under Catalysis. Well-Defined
Supporting Information for the Paper Sequential Addition of Phosphine to Alkynes for the Selective Synthesis of 1,2-Diphosphinoethanes under Catalysis. Well-Defined NHC-Copper Phosphides vs in Situ CuCl
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation
Διαβάστε περισσότεραAsymmetric H/D exchange reaction of fluorinated aromatic ketones
Asymmetric H/D exchange reaction of fluorinated aromatic ketones Yujun Zhao 1 Xiaozhi Lim 2 Yuanhang Pan 1 Lili Zong 1 Wei Feng 1 and Choon-Hong Tan 1 * Kuo-Wei Huang 2 * 1 Department of Chemistry and
Διαβάστε περισσότεραElectronic Supplementary Information
7- Selenabicyclo[2.2.1]heptane Phoebe E. Macdougall, a,b Heather M. Aitken, a,b Peter J. Scammells, a,c Yvonne Kavanagh, a,b Sara H. Kyne, a,b,d and Carl H. Schiesser* a,b Electronic Supplementary Information
Διαβάστε περισσότεραSupporting information
Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition
Διαβάστε περισσότεραSupporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic
Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long
Διαβάστε περισσότεραPt-Ag Clusters and their Neutral Mononuclear Pt(II) Starting Complexes: Structural and Luminescence Studies.
Pt-Ag Clusters and their Neutral Mononuclear Pt(II) Starting Complexes: Structural and Luminescence Studies. Juan Forniés* a, Violeta Sicilia *b, José Mª Casas a, Antonio Martín a, José A. López a, Carmen
Διαβάστε περισσότεραDirect Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3
Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate
Διαβάστε περισσότεραFree Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2
Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan
Διαβάστε περισσότερα9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer
Διαβάστε περισσότεραSUPPORTING INFORMATION. Visible Light Excitation of a Molecular Motor with an Extended Aromatic Core
SUPPORTING INFORMATION Visible Light Excitation of a Molecular Motor with an Extended Aromatic Core Thomas van Leeuwen, Jasper Pol, Diederik Roke, Sander J. Wezenberg, Ben L. Feringa* Stratingh Institute
Διαβάστε περισσότεραSupporting Information. Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors
Supporting Information Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors Frédéric Pin, a Frédéric Buron, a Fabienne Saab, a Lionel Colliandre,
Διαβάστε περισσότεραFluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine
Διαβάστε περισσότεραSupporting Information
Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
Διαβάστε περισσότεραSynthesis and evaluation of novel aza-caged Garcinia xanthones
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Synthesis and evaluation of novel aza-caged Garcinia xanthones Xiaojin Zhang, a,1 Xiang Li, a,1 Haopeng Sun, * b Zhengyu Jiang,
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple
Διαβάστε περισσότεραPeptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors
Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors Andrea Trabocchi a, icolino Pala b, Ilga Krimmelbein c, Gloria Menchi a, Antonio Guarna a, Mario Sechi b, Tobias Dreker c, Andrea Scozzafava
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Polymer hemistry This journal is The Royal Society of hemistry 2011 Phosphoric and Phosphoramidic Acids as Bifunctional atalysts for the Ring-pening Polymerization
Διαβάστε περισσότεραSupporting Material. Hydrogen Oxidation and Production Using Nickel-Based Molecular Catalysts with Positioned Proton Relays
Supporting Material Hydrogen Oxidation and Production Using Nickel-Based Molecular Catalysts with Positioned Proton Relays Aaron D. Wilson, Rachel H. Newell, Michael J. McNevin, James T. Muckerman, ψ M.
Διαβάστε περισσότεραSupplementary Figures
Supplementary Figures Supplementary Figure 1. 1 H NMR spectrum (400 MHz, CDCl 3 ) of diester 3. Supplementary Figure 2. 13 C NMR spectrum (100 MHz, CDCl 3 ) of diester 3. 1 Supplementary Figure 3. 1 H
Διαβάστε περισσότεραTributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate
upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic
Διαβάστε περισσότεραRegioselective and Stereospecific Cu-Catalyzed Deoxygenation of Epoxides to Alkenes
Supporting Information Regioselective and Stereospecific Cu-Catalyzed Deoxygenation of Epoxides to Alkenes Jingxun Yu, Yu Zhou, Zhenyang Lin*, and Rongbiao Tong* Table of Contents General Information S-2
Διαβάστε περισσότεραSupplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry Supporting Information
Supporting Information Unexpected Nucleophilic Behaviour of Radicals Generated from α-iodoketones Corinne De Dobbeleer, a Ji í Pospíšil, a Freija De Vleeschouwer, b Frank De Proft b and István E. Markó
Διαβάστε περισσότεραSupporting Information. Fluorinated Thiophene-Based Synthons: Polymerization of 1,4-Dialkoxybenzene
Supporting Information Fluorinated Thiophene-Based Synthons: Polymerization of 1,4-Dialkoxybenzene and Fluoro-Dithieno-2,1,3-benzothiadiazole by Direct Heteroarylation Carl Roy, 1 Thomas Bura, 1, Serge
Διαβάστε περισσότεραPhosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions
Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a
Διαβάστε περισσότεραEffect of uridine protecting groups on the diastereoselectivity
Supporting Information for Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5 -alkynylation Raja Ben Othman, Mickaël J. Fer, Laurent Le Corre, Sandrine Calvet-Vitale*
Διαβάστε περισσότεραSupporting Information
S1 Supporting Information Synthesis of 2-Arylated Hydroxytyrosol Derivatives via Suzuki-Myaura Cross-Coupling Roberta Bernini, a Sandro Cacchi, b* Giancarlo Fabrizi, b* Eleonora Filisti b a Dipartimento
Διαβάστε περισσότεραSupplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene
Διαβάστε περισσότεραSupporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors
Supporting Information Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors Xiao-Peng He, abd Cui Li, d Xiao-Ping Jin, b Zhuo Song, b Hai-Lin Zhang,
Διαβάστε περισσότεραExperimental and Theoretical Evidence of the Au(I) Bi(III) Closed-Shell Interaction
Experimental and Theoretical Evidence of the Au(I) Bi(III) Closed-Shell Interaction Eduardo J. Fernández, a * Antonio Laguna, b * José M. López-de-Luzuriaga, a Miguel Monge, a M. Elena Olmos, a Mihai Nema,
Διαβάστε περισσότεραSupporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction
Supporting Information ne-pot Approach to Chiral Chromenes via Enantioselective rganocatalytic Domino xa-michael-aldol Reaction Hao Li, Jian Wang, Timiyin E-Nunu, Liansuo Zu, Wei Jiang, Shaohua Wei, *
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Supporting Information for Catalytic Enantioselective Conjugate Reduction of β,β- Disubstituted α,β-unsaturated sulfones Tomás Llamas, Ramón
Διαβάστε περισσότεραMetal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:
Διαβάστε περισσότεραDiastereoselective Access to Trans-2-Substituted Cyclopentylamines
Supporting Information Diastereoselective Access to Trans-2-Substituted Cyclopentylamines Antoine Joosten, Emilie Lambert, Jean-Luc Vasse, Jan Szymoniak jean-luc.vasse@univ-reims.fr jan.szymoniak@univ-reims.fr
Διαβάστε περισσότεραSupporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Jincan Zhao 1, Hong Fang 1, Jianlin Han* 1,2 and Yi Pan* 1
Διαβάστε περισσότεραRegioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.
Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section
Διαβάστε περισσότεραSynthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of
Διαβάστε περισσότεραSupporting Information
Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,
Διαβάστε περισσότεραSculpting the β-peptide foldamer H12 helix via a designed side chain shape
SUPPLEMENTARY DATA Sculpting the β-peptide foldamer H12 helix via a designed side chain shape Anasztázia Hetényi, a Zsolt Szakonyi, a István M. Mándity, a Éva Szolnoki, a Gábor K. Tóth, b Tamás A. Martinek,*
Διαβάστε περισσότερα