PS-BEMP as a Basic Catalyst for the Phospha-Michael Addition to Electron-poor alkenes
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- Ιλαρίων Μπότσαρης
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 SUPPORTING INFORMATION PS-BEMP as a Basic Catalyst for the Phospha-Michael Addition to Electron-poor alkenes Giacomo Strappaveccia, a Luca Bianchi, a Simone Ziarelli, a Stefano Santoro*, a Daniela Lanari, b Ferdinando Pizzo a and Luigi Vaccaro* a a CEMIN - Centro di Eccellenza Materiali Innovativi Nanostrutturati Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Perugia Via Elce di Sotto, 8 I , Perugia, Italia b Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo, Perugia, Italia. Fax: (+39) luigi.vaccaro@unipg.it; stefano.santoro@unipg.it CONTENTS ESI 2 ESI 3 ESI 4 - ESI 23 Experimental Section Representative GLC analysis Full characterization data ( 1 H NMR, 13 C NMR, 31 P NMR, GC-EIMS) for compounds 4a-f, 7a-g, 12a-d and 13a-d ESI 24 - ESI 83 Copies of the 1 H, 13 C and 31 P NMR for compounds 4a-f, 7a-g, 12a-d and 13a-d ESI - 1
2 Experimental Section Unless otherwise stated, all chemicals were purchased and used without any further purification. GLC analyses were performed by using a Hewlett-Packard HP 5890A equipped with a capillary column DB-35MS (30 m, 0.53 mm), a FID detector and helium as gas carrier. GC-EIMS analyses were carried out by using a Hewlett-Packard HP 6890N Network GC system/5975 Mass Selective Detector equipped with an electron impact ionizer at 70 ev. All 1 H NMR, 13 C NMR and 31 P NMR spectra were recorded at 400 MHz, MHz and MHz, respectively, using a Bruker DRX-ADVANCE 400 MHz spectrometer. The deuterated solvent used was CDCl 3, and TMS was employed as internal standard. Chemical shifts are reported in ppm and coupling constants in hertz. Elemental analyses were realized by using a FISONS instrument EA 1108 CHN. Compounds 3a, 1 3b-d, 2 7a, 3 7b, 4 7e, 5 7g, 6 12a, 7 12b, 8 12c, 9 12d, 9 13a 10 and 13b 1 are known, while compounds 3e-f, 7d, 7f, 13c and 13d are unknown. References 1. D. Semenzin, G. Etemad-Moghadam, D. Albouy, O. Diallo and M. Koenig, J. Org. Chem., 1997, 62, A. Zhang, L. Cai, Z. Yao, F. Xu and Q. Shen, Heteroat. Chem., 2013, 24, E. Öhler and E. Zbiral, Liebigs Ann. Chem., 1991, 3, D. Zhao, Y. Yuan, A. S. C. Chan and R. Wang, Chem. Eur. J., 2009, 15, D. Simoni, F. P. Invidiata, M. Manferdini, I. Lampronti, R. Rondanin, M. Roberti and G. P. Pollini, Tetrahedron Lett., 1998, 39, I. Mori, Y. Kimura, T. Nakano, S. Matsunaga, G. Iwasaki, A. Ogawa and K. Hayakawa, Tetrahedron Lett., 1997, 38, (a) T. Wüster, N. Kaczybura, R. Brückner and M. Keller, Tetrahedron, 2013, 69, ; (b) S. Olagnon-Bourgeot, F. Chastrette and D. Wilhelm, Magn. Reson. Chem., 1995, 33, E. Martínez-Castro, O. López, I. Maya, J. G. Fernández-Bolanõs and M. Petrini, Green Chem., 2010, 12, R. Kadyrov, R. Selke, R. Giernoth and J. Bargon, Synthesis, 1999, B. C. Ranu and S. Samanta, Tetrahedron, 2003, 59, ESI - 2
3 GLC analysis of the reaction mixture of 1 with 2 giving a 70:30 mixture of compounds 3a and 3a' (Table 1 entry 11). ESI - 3
4 Chem. Name Diethyl (3-oxo-1-phenylbutyl)phosphonate (3a) Lit. Ref. J. Org. Chem. 1997, 62, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-4-phenylbut-3-en-2-one (1a) (75 mg, 0.5 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 60 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 3a was obtained as an oil (114 mg, 80% yield). Mol Formula C 14 H 21 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 59.15; H: 7.45; found C: 60.35; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz t t s m m m m m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.8 Hz); (d, j P-C = 5.9 Hz); 30.28; (d, j P-C = 140 Hz); 43.68; (d, j P-C = 7.1 Hz); (d, j P-C = 6.8 Hz);127.22; ; (d, j P-C = 6.4 Hz); (d, j P-C = 6.8 Hz), (d, j P-C = 14.4 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 284 (M +, 12); 242 (15); 241 (100); 213 (23); 185 (53); 138 (16); 129 (12); 111 (20); 104 (29); 103 (23); 81 (13); 78 (12); 77 (14); 43 (60) ESI - 4
5 Chem. Name Diethyl (3-oxo-1,3-diphenylpropyl)phosphonate (3b) Lit. Ref. Heteroat. Chem. 2013, 24, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-chalcone (1b) (106 mg, 0.5 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 3b was obtained as an oil (142 mg, 82% yield). Mol Formula C 19 H 23 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 65.89; H: 6.69; found C: 65.78; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz t t m m m m m m d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.5 Hz); (d, j P-C = 5.9 Hz); 38.9 (d, j P-C = 140 Hz); 39.01; (d, j P-C = 7.1 Hz); (d, j P-C = 6.7 Hz); ; ; ; ; (d, j P-C = 6.5 Hz), ; (d, j P-C = 6.7 Hz); ; (d, j P-C = 14.9 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 346 (M +, 8); 242 (13); 241 (99); 213 (15); 185 (36); 105 (100); 104 (30); 103 (21); 81 (14); 78 (15); 77( 76); 51 (14) ESI - 5
6 Chem. Name Diethyl (1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)phosphonate (3c) Lit. Ref. Heteroat. Chem. 2013, 24, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (1c) (121 mg, 0.5 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 36 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 3c was obtained as an oil (148 mg, 78% yield). Mol Formula C 19 H 22 ClO 4 P m.p. Oil Elemental Analysis: Calc.: C: 59.93; H: 5.82; found C: 59.88; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz t t m m m m m m d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.6 Hz); (d, j P-C = 5.8 Hz); (d, j P-C = 141 Hz); 38.92; (d, j P-C = 7.0 Hz); (d, j P-C = 6.8 Hz); ; ; (d, j P-C = 6.5 Hz); ; ; (d, j P-C = 6.9 Hz); ; (d, j P-C = 15.4 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 382 (M + +2,2); 380 (M +, 8); 277 (27); 275 (80); 219 (33); 138 (24); 105 (100); 77 (86) ESI - 6
7 Chem. Name Diethyl (1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl)phosphonate (3d) Lit. Ref. Heteroat. Chem. 2013, 24, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (1d) (119 mg, 0.5 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 3d was obtained as an oil (152 mg, 81% yield). Mol Formula C 20 H 25 O 5 P m.p. Oil Elemental Analysis: Calc.: C: 63.82; H: 6.69; found C: 63.92; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz t t m m m d m m m d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.7 Hz); (d, j P-C = 5.9 Hz); (d, j P-C = 141 Hz); 39.10; 55.07; (d, j P-C = 7.2 Hz); (d, j P-C = 6.9 Hz); ; (d, j P-C = 6.9 Hz); ; ; (d, j P-C = 6.5 Hz); ; ; ; (d, j P-C = 15.3 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 376 (M +, 16); 271 (100); 243 (18); 215 (37); 134 (18); 133 (14); 105 (83); 77 (45) ESI - 7
8 Chem. Name Diethyl (4-oxo-4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-yl)phosphonate (3e) Lit. Ref. / METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one (1e) (106 mg, ml, 0.5 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 48 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 3e was obtained as an oil (132 mg, 80% yield). Mol Formula C 17 H 31 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 61.80; H: 9.46; found C: 61.81; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz s s m t m s m m m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.1 Hz); (d, j P-C = 5.6 Hz); 18.46; 20.34; (d, j P-C = 144 Hz); 28.33; 30.85; 32.94; 38.52; 45.67; (d, j P-C = 6.7 Hz); (d, j P-C = 6.7 Hz); ; ; (d, j P-C = 15.9 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 330 (M + ; 15); 207 (63); 180 (15); 179 (50); 151 (100); 123 (17); 81 (24); 69 (53) ESI - 8
9 Chem. Name Diethyl (4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl)phosphonate (3f) Lit. Ref. / METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (1f) (106 mg, ml, 0.5 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 48 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 3f was obtained as an oil (ca. 1:1 diasteroisomeric mixture) (135 mg, 82% yield). Mol Formula C 17 H 31 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 61.80; H: 9.46; found C: 61.90; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz s s m t m m m m m s 13 C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 7.7 Hz); 16.24; 22.44; 23.20; (d, j P-C = Hz); 27.62; 30.49; 32.28; 46.00; (d, j P-C = 6.9 Hz); (d, j P-C = 6.5 Hz); 63.00; ; ; (d, j P-C = Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 330 (M +, 22); 207 (27); 179 (34); 166 (48); 165 (53); 151 (100); 138 (21); 123 (62); 109 (28); 93 (24); 91 (29); 81 (79); 79 (27); 69 (53); 67 (18); 65 (19); 55 (23); 43 (25) ESI - 9
10 Chem. Name Dimethyl (3-oxo-1-phenylbutyl)phosphonate (7a) Lit. Ref. Liebigs Ann. Chem. 1991, 3, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-4-phenylbut-3-en-2-one (1a) (75 mg, 0.5 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 7a was obtained as an oil (105 mg, 82% yield). Mol Formula C 12 H 19 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 56.25; H: 6.69; found C: 57.35; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz s m d d m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 30.19; (d, j P-C = Hz); 43.52; (d, j P-C = 7.1 Hz); (d, j P-C = 6.7 Hz); (d, j P-C = 2.6 Hz); ; (d, j P-C = 6.5 Hz); (d, j P-C = 7.0 Hz); (d, j P-C = 14.0 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 256 (M +, 9); 214 (14); 213 (100); 110 (19); 104 (16); 103 (21); 43 (26) ESI - 10
11 Chem. Name Dimethyl (3-oxo-1,3-diphenylpropyl)phosphonate (7b) Lit. Ref. Chem. Eur. J. 2009, 15, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-chalcone (1b) (106 mg, 0.5 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 7b was obtained as an oil (135 mg, 85% yield). Mol Formula C 17 H 19 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 64.15; H: 6.02; found C: 64.38; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz d m m m m m m d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = Hz); 38.94; (d, j P-C = 7.2 Hz); (d, j P- C= 6.8 Hz); ; ; ; (d, j P-C = 6.5 Hz); ; (d, j P-C = 6.9 Hz); ; (d, j P-C = 15.0 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 318 (M +, 8); 214 (12); 213 (100); 105 (48); 104 (11); 103 (15); 77 (35) ESI - 11
12 Chem. Name Dimethyl (1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl)phosphonate (7d) Lit. Ref. / METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (1d) (119 mg, 0.5 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 7d was obtained as an oil (144 mg, 83% yield). Mol Formula C 18 H 21 O 5 P m.p. Oil Elemental Analysis: Calc.: C: 62.07; H: 6.08; found C: 62.22; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz d m m d m m m d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = Hz); 39.02; (d, j P-C = 7.3 Hz); (d, j P- C= 6.8 Hz); 55.03; ; (d, j P-C = 6.9 Hz); ; ; (d, j P-C = 6.5 Hz); ; ; ; (d, j P-C = 15.2 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 348 (M +, 13); 244 (13); 242 (100); 134 (10); 133 (20); 105 (42); 77 (28) ESI - 12
13 Chem. Name Dimethyl (4-oxo-4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-yl)phosphonate (7e) Lit. Ref. Tetrahedron Lett. 1998, 39, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one (1e) (106 mg, ml, 0.5 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 48 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 7e was obtained as an oil (121 mg, 80% yield). Mol Formula C 15 H 27 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 59.59; H: 9.00; found C: 59.69; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz s s m m s m t m m d d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.2 Hz); 19.13; 21.05; (d, j P-C = Hz); 29.04; 31.56; 33.66; 39.21; 46.27; (d, j P-C = 6.7 Hz); (d, j P-C = 6.7 Hz); ; ; (d, j P-C = 15.9 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 302 (M +, 21); 179 (100); 165 (55); 151 (89); 138 (24); 123 (59); 110 (31); 109 (51), 95 (19); 93 (32); 91 (25); 81 (66); 79 (50); 69 (68); 55 (26); 43 (22) ESI - 13
14 Chem. Name Dimethyl (4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl)phosphonate (7f) Lit. Ref. / METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (1f) (106 mg, ml, 0.5 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 48 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 7f was obtained as an oil (ca. 1:1 diasteroisomeric mixture) (124 mg, 82% yield). Mol Formula C 15 H 27 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 59.59; H: 9.00; found C: 59.50; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz 0.85 and two s (diasteroisomeric mixture) 0.88 and two s (diasteroisomeric mixture) m dd 8.0; s m d d s 13 C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 13.0 Hz); 22.97; 23.76; (d, j P-C = Hz); 28.19; 31.08; 32.80; 46.96; (d, j P-C = 7.1. Hz); (d, j P-C = 7.0 Hz); 63.64; ; ; (d, j P-C = 33.2 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : 32.1 GC-EIMS (m/z, %): 302 (M +, 7); 179 (100); 110 (18); 109 (23); 101 (22); 93 (22); 79 (20); 69 (68) ESI - 14
15 Chem. Name Dimethyl (3-oxocyclohexyl)phosphonate (7g) Lit. Ref. Tetrahedron Lett. 1997, 38, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), cyclohex-2-enone (1g) (51 mg, ml, 0.5 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 60 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 7g was obtained as an oil (79 mg, 80% yield). Mol Formula C 8 H 15 O 4 P m.p. Oil Elemental Analysis: Calc.: C: 46.60; H: 7.33; found C: 46.65; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz m m d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 4.4 Hz); 25.90; (d, j P-C = Hz); (d, j P- C= 5.0 Hz); 40.96; (d, j P-C = 6.9 Hz); (d, j P-C = 16.7 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 206 (M +, 39); 163 (26); 137 (100); 111 (48); 110 (59); 109 (31); 97 (65); 96 (71); 95 (19); 80 (25); 79 (37); 69 (19); 55 (30) ESI - 15
16 Chem. Name Methyl 3-(dimethoxyphosphoryl)propanoate (12a) Lit. Ref. Tetrahedron, 2013, 69, ; Magn. Reson. Chem., 1995, 33, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), methyl acrylate (10a) (86 mg, ml, 1 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 12a was obtained as an oil (83 mg, 85% yield). Mol Formula C 6 H 13 O 5 P m.p. Oil Elemental Analysis: Calc.: C: 36.74; H: 6.68; found C: 36.78; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz m m s d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = Hz); (d, j P-C = 3.9 Hz); 52.02; (d, j P- C= 6.4 Hz); (d, j P-C = 19.2 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 196 (M +,6); 165 (100); 164 (33); 137 (51); 110 (59); 109 (83); 105 (13); 93 (18); 87 (10); 80 (12); 79 (35); 55 (21). ESI - 16
17 Chem. Name Methyl 3-(diethoxyphosphoryl)propanoate (12b) Lit. Ref. Green Chem., 2010, 12, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), methyl acrylate (10a) (86 mg, ml, 1 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 12b was obtained as an oil (88 mg, 79% yield). Mol Formula C 8 H 17 O 5 P m.p. Oil Elemental Analysis: Calc.: C: 42.86; H: 7.64; found C: 42.90; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz t m m s m 13 C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.9 Hz); (d, j P-C = Hz); (d, j P-C = 3.4 Hz); 51.96; (d, j P-C = 6.2 Hz); (d, j P-C = 18.8 Hz ) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 224 (M +, 4);197 (13), 193 (17); 192 (10); 179 (16); 165 (100); 151 (34); 138 (42); 137 (93); 123 (10) 111 (16); 109 (31); 95 (11); 91 (10); 81 (17); 65 (10); 55 (24) ESI - 17
18 Chem. Name Methyl 3-(dimethoxyphosphoryl)butanoate (12c) Lit. Ref. Synthesis, 1999, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), methyl crotonate (10b) (100 mg, ml, 1 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 12c was obtained as an oil (36 mg, 34% yield). Mol Formula C 7 H 15 O 5 P m.p. Oil Elemental Analysis: Calc.: C: 40.01; H: 7.19; found C: 40.22; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz dd 6.9; m m m s d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 4.4 Hz); (d, j P-C = Hz); 35.00; 51.89; (d, j P-C = 6.8 Hz); (d, j P-C = 6.8 Hz); (d, j P-C = 18.9 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 210 (M +, 5); 179 (52); 151 (100); 150 (11); 137 (44); 124 (10); 119 (12);110 (64); 109 (54); 101 (13); 93 (10); 80 (14); 79 (30); 69 (23) ESI - 18
19 Chem. Name Methyl 3-(diethoxyphosphoryl)butanoate (12d) Lit. Ref. Synthesis, 1999, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), methyl crotonate (10b) (100 mg, ml, 1 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 12d was obtained as an oil (62 mg, 52% yield). Mol Formula C 9 H 19 O 5 P m.p. Oil Elemental Analysis: Calc.: C: 45.38; H: 8.04; found C: 45.12; H: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz dd 6.9; t m m s m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 13.60(d, j P-C = 5.2 Hz); (d, j P-C = 5.8 Hz); (d, j P-C = Hz); 35.12; 51.84; (d, j P-C = 6.8 Hz); (d, j P-C = 7.5 Hz); (d, j P-C = 19.0 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 238 (M +, 3); 207 (22); 193 (13); 179 (100); 165 (40); 152 (11); 151 (55); 138 (62); 137 (10); 123 (22); 111 (41); 110 (12); 109 (23); 87 (12); 82 (16); 81 (20); 69 (49); 65 (12); 59 (16) ESI - 19
20 Chem. Name Dimethyl (2-cyanoethyl)phosphonate (13a) Lit. Ref. Tetrahedron, 2003, 59, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), acrylonitrile (11a) (53 mg, ml, 1 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 13a was obtained as an oil (73 mg, 90% yield). Mol Formula C 5 H 10 NO 3 P m.p. Oil Elemental Analysis: Calc.: C: 36.82; H: 6.18; N: 8.59; found C: 36.61; H: 6.04; N: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz m m d C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 4.4 Hz); (d, j P-C = Hz); (d, j P-C = 6.5 Hz); (d, j P-C = 17.5 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 163 (M +, 4); 132 (10); 110 (100); 109 (100); 95 (11); 80 (14); 79 (47); 68 (12); 47 (11) ESI - 20
21 Chem. Name Diethyl (2-cyanoethyl)phosphonate (13b) Lit. Ref. J. Org. Chem., 1997, 62, METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), acrylonitrile (11a) (53 mg, ml, 1 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 95/5). 13b was obtained as an oil (85 mg, 89% yield). Mol Formula C 7 H 14 NO 3 P m.p. Oil Elemental Analysis: Calc.: C: 43.98; H: 7.38; N: 7.33; found C: 44.12; H: 7.50; N: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz t m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 3.6 Hz); (d, j P-C = 5.7 Hz); (d, j P-C = Hz); (d, j P-C = 6.4 Hz); (d, j P-C = 18.1 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 191 (M +, 4); 164 (50); 146 (11); 138 (12); 136 (100); 135 (15); 118 (25); 109 (14); 82 (11); 81 (12); 54 (22) ESI - 21
22 Chem. Name Dimethyl (2-cyano-1-phenylethyl)phosphonate (13c) Lit. Ref. / METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), cinnamonitrile (11b) (129 mg, ml, 1 mmol), and dimethyl phosphite (4) (61 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 70/30). 13c was obtained as an oil (91 mg, 76% yield). Mol Formula C 11 H 14 NO 3 P m.p. Oil Elemental Analysis: Calc.: C: 55.23; H: 5.90; N: 5.86; found C: 55.48; H: 6.02; N: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz m ddd 22.0; 10.4; d d m 13 C NMR (100.6 MHz, CDCl 3 ) δ : 19.53; (d, j P-C = Hz); (d, j P-C = 7.2 Hz); (d, j P- C= 6.9 Hz); (d, j P-C = 19.6 Hz); ; (d, j P-C = 6.6 Hz); ; (d, j P-C = 6.6 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 239 (M +, 68); 238 (10); 224 (27); 207 (13); 131 (11); 130 (100); 129 (12); 128 (10); 110 (93); 109 (36); 104 (72); 103 (47); 102 (15); 93 (14); 80 (13); 79 (19); 78 (12); 77 (32) ESI - 22
23 Chem. Name Diethyl (2-cyano-1-phenylethyl)phosphonate (13d) Lit. Ref. / METHOD: In a screw capped vial equipped with a magnetic stirrer PS-BEMP (43 mg, 0.1 mmol, 2.13 mmol/g), cinnamonitrile (11b) (129 mg, ml, 1 mmol), and diethyl phosphite (2) (70 mg, ml, 0.5 mmol) were consecutively added and the resulting mixture was left under stirring at 80 C. After 24 hours EtOAc (1 ml) was added and the catalyst was filtered off and the solvent was removed under vacuum. The obtained oil was purified by flash column chromatography on silica gel (petroleum ether/etoac 70/30). 13d was obtained as an oil (115 mg, 86% yield). Mol Formula C 13 H 18 NO 3 P m.p. Oil Elemental Analysis: Calc.: C: 58.42; H: 6.79; N: 5.24; found C: 58.61; H: 6.64; N: H NMR 400 MHz CDCl 3 value No. H Mult. j value/hz t t m ddd 21.6; 10.4; m m m m 13 C NMR (100.6 MHz, CDCl 3 ) δ : (d, j P-C = 5.6 Hz); (d, j P-C = 5.9 Hz); 19.60; (d, j P-C = Hz); (d, j P-C = 5.6 Hz); (d, j P-C = 6.9 Hz); (d, j P-C = 19.8 Hz); ; (d, j P-C = 6.3 Hz); ; (d, j P-C = 6.6 Hz) 31 P NMR (161.9 MHz, CDCl 3 ) δ : GC-EIMS (m/z, %): 267 (M +, 42); 238 (14); 211 (13); 210 (10); 138 (36); (10); 130 (65); 129 (10); 111 (20); 109 (21); 105 (11); 104 (100); 103 (41); 102 (10); 91 (14); 81 (15); 77 (24) ESI - 23
24 Diethyl (3 oxo 1 phenylbutyl)phosphonate (3a) ppm ESI - 24
25 Diethyl (3 oxo 1 phenylbutyl)phosphonate (3a) ppm ESI - 25
26 Diethyl (3 oxo 1 phenylbutyl)phosphonate (3a) ppm ESI - 26
27 ppm Diethyl (3 oxo 1,3 diphenylpropyl)phosphonate (3b) ESI - 27
28 Diethyl (3-oxo-1,3-diphenylpropyl)phosphonate (3b) ppm ESI - 28
29 Diethyl (3 oxo 1,3 diphenylpropyl)phosphonate (3b) ppm ESI - 29
30 Diethyl (1 (4 chlorophenyl) 3 oxo 3 phenylpropyl)phosphonate (3c) ppm ESI - 30
31 Diethyl (1 (4 chlorophenyl) 3 oxo 3 phenylpropyl)phosphonate (3c) ppm ESI - 31
32 Diethyl (1 (4 chlorophenyl) 3 oxo 3 phenylpropyl)phosphonate (3c) ppm ESI - 32
33 Diethyl (1 (4 methoxyphenyl) 3 oxo 3 phenylpropyl)phosphonate (3d) ppm ESI - 33
34 Diethyl (1 (4 methoxyphenyl) 3 oxo 3 phenylpropyl)phosphonate (3d) ppm ESI - 34
35 Diethyl (1 (4 methoxyphenyl) 3 oxo 3 phenylpropyl)phosphonate (3d) ppm ESI - 35
36 Diethyl (4 oxo 4 (2,6,6 trimethylcyclohex 1 en 1 yl)butan 2 yl)phosphonate (3e) ppm ESI - 36
37 Diethyl (4 oxo 4 (2,6,6 trimethylcyclohex 1 en 1 yl)butan 2 yl)phosphonate (3e) ppm ESI - 37
38 Diethyl (4 oxo 4 (2,6,6 trimethylcyclohex 1 en 1 yl)butan 2 yl)phosphonate (3e) ppm ESI - 38
39 Diethyl (4 oxo 4 (2,6,6 trimethylcyclohex 2 en 1 yl)butan 2 yl)phosphonate (3f) ppm ESI - 39
40 Diethyl (4 oxo 4 (2,6,6 trimethylcyclohex 2 en 1 yl)butan 2 yl)phosphonate (3f) ppm ESI - 40
41 Diethyl (4 oxo 4 (2,6,6 trimethylcyclohex 2 en 1 yl)butan 2 yl)phosphonate (3f) ppm ESI - 41
42 Dimethyl (3 oxo 1 phenylbutyl)phosphonate (7a) ppm ESI - 42
43 Dimethyl (3 oxo 1 phenylbutyl)phosphonate (7a) ppm ESI - 43
44 Dimethyl (3 oxo 1 phenylbutyl)phosphonate (7a) ppm ESI - 44
45 Dimethyl (3 oxo 1,3 diphenylpropyl)phosphonate (7b) ppm ESI - 45
46 Dimethyl (3 oxo 1,3 diphenylpropyl)phosphonate (7b) ppm ESI - 46
47 Dimethyl (3 oxo 1,3 diphenylpropyl)phosphonate (7b) ppm ESI - 47
48 Dimethyl (1 (4 methoxyphenyl) 3 oxo 3 phenylpropyl)phosphonate (7d) ppm ESI - 48
49 Dimethyl (1 (4 methoxyphenyl) 3 oxo 3 phenylpropyl)phosphonate (7d) ppm ESI - 49
50 Dimethyl (1 (4 methoxyphenyl) 3 oxo 3 phenylpropyl)phosphonate (7d) ppm ESI - 50
51 Dimethyl (4 oxo 4 (2,6,6 trimethylcyclohex 1 en 1 yl)butan 2 yl)phosphonate (7e) ppm ESI - 51
52 Dimethyl (4 oxo 4 (2,6,6 trimethylcyclohex 1 en 1 yl)butan 2 yl)phosphonate (7e) ppm ESI - 52
53 Dimethyl (4 oxo 4 (2,6,6 trimethylcyclohex 1 en 1 yl)butan 2 yl)phosphonate (7e) ppm ESI - 53
54 Dimethyl (4 oxo 4 (2,6,6 trimethylcyclohex 2 en 1 yl)butan 2 yl)phosphonate (7f ) ppm ESI - 54
55 Dimethyl (4 oxo 4 (2,6,6 trimethylcyclohex 2 en 1 yl)butan 2 yl)phosphonate (7f ) ppm ESI - 55
56 Dimethyl (4 oxo 4 (2,6,6 trimethylcyclohex 2 en 1 yl)butan 2 yl)phosphonate (7f ) ppm ESI - 56
57 Dimethyl (3 oxocyclohexyl)phosphonate (7g) ppm ESI - 57
58 Dimethyl (3 oxocyclohexyl)phosphonate (7g) ppm ESI - 58
59 Dimethyl (3 oxocyclohexyl)phosphonate (7g) ppm ESI - 59
60 Methyl 3-(dimethoxyphosphoryl)propanoate (12a) ppm ESI - 60
61 Methyl 3-(dimethoxyphosphoryl)propanoate (12a) ppm ESI - 61
62 Methyl 3-(dimethoxyphosphoryl)propanoate (12a) ppm ESI - 62
63 Methyl 3-(diethoxyphosphoryl)propanoate (12b) ppm ESI - 63
64 Methyl 3-(diethoxyphosphoryl)propanoate (12b) ppm ESI - 64
65 Methyl 3-(diethoxyphosphoryl)propanoate (12b) ppm ESI - 65
66 Methyl 3-(dimethoxyphosphoryl)butanoate (12c) ppm ESI - 66
67 Methyl 3-(dimethoxyphosphoryl)butanoate (12c) ppm ESI - 67
68 Methyl 3-(dimethoxyphosphoryl)butanoate (12c) ppm ESI - 68
69 Methyl 3-(diethoxyphosphoryl)butanoate (12d) ppm ESI - 69
70 Methyl 3-(diethoxyphosphoryl)butanoate (12d) ppm ESI - 70
71 Methyl 3-(diethoxyphosphoryl)butanoate (12d) ppm ESI - 71
72 Dimethyl (2-cyanoethyl)phosphonate (13a) ppm ESI - 72
73 Dimethyl (2-cyanoethyl)phosphonate (13a) ppm ESI - 73
74 Dimethyl (2-cyanoethyl)phosphonate (13a) ppm ESI - 74
75 Diethyl (2-cyanoethyl)phosphonate (13b) ppm ESI - 75
76 Diethyl (2-cyanoethyl)phosphonate (13b) ppm ESI - 76
77 Diethyl (2-cyanoethyl)phosphonate (13b) ppm ESI - 77
78 Dimethyl (2-cyano-1-phenylethyl)phosphonate (13c) ppm ESI - 78
79 Dimethyl (2-cyano-1-phenylethyl)phosphonate (13c) ppm ESI - 79
80 Dimethyl (2-cyano-1-phenylethyl)phosphonate (13c) ppm ESI - 80
81 Diethyl (2-cyano-1-phenylethyl)phosphonate (13d) ppm ESI - 81
82 Diethyl (2-cyano-1-phenylethyl)phosphonate (13d) ppm ESI - 82
83 Diethyl (2-cyano-1-phenylethyl)phosphonate (13d) ppm ESI - 83
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