Eur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 ISSN X SUPPORTING INFORMATION
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1 Eur. J. rg. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 ISSN X SUPPRTING INFRMATIN Title: ne-pot Synthesis of xo Acid Derivatives by Rh I -Catalyzed Chelation-Assisted Hydroacylation Author(s): Eun-Ae Jo, Chul-Ho Jun* Ref. No.:
2 General Experiments. Flash column chromatography was performed using E. Merck mesh silica gel. Column chromatography were monitored by analytical thinlayer chromatography (TLC) carried out on 0.25 mm E. Merck silica gel plates (60 F- 254) using UV light as a visualizing agent and p-anisaldehyde solution, and heat as developing agent. Gas chromatographic analyses were performed on a Donam DS 6200 instrument with FID detector and a Hewlett Packard HP-5 capillary column. Lowresolution mass spectra were measured on a Hewlett-Packard HP G1800A GCD system equipped with a Hewlett Packard HP-5 capillary column. NMR spectra were recorded in CDCl 3 on Bruker Avance DPX 250 spectrometer ( 1 H NMR, 250 MHz; 13 C NMR, 62.9 MHz) spectrometer, and the chemical shift was expressed in ppm relative to TMS. IR spectra were recorded on Nicolet Impact 400 spectrometer. Elemental Analysis (EA) was obtained from the rganic Chemistry Research Center, Sogang University, Seoul, Korea. High-resolution mass spectrometry was performed by the National Center for Inter-University Facilities, Seoul National University, Seoul, Korea. Materials. (PPh 3 ) 3 RhCl (3) was prepared as described in the literature. 1 Aldehyde and olefins used in the experiments were purchased from commercial sources (Aldrich Chemical Company) and purified by standard procedures. 2 Toluene was distilled from sodium/benzophenone under nitrogen atmosphere prior to use. Typical Procedure for Hydroacylation. (Table 1, entry 1) A screw-capped pressure vial (1 ml) was charged with 26.5 mg (0.25 mmol) of benzaldehyde (1a), 43 mg (0.5 mmol) of methyl acrylate (2a), 11.6 mg ( mmol) of (PPh 3 ) 3 RhCl (3), 10.8 mg (0.1 mmol) of 2-amino-3-picoline (4), 6.1 mg (0.05 mmol) of benzoic acid (5) and 80 mg of toluene. The reaction mixture was stirred in an oil bath that was preheated at 130 C for 1h. After cooling to room temperature, the organic layer was extracted with 1 J. A. sborn, G. Wilkinson, In Reagents for Transition Metal Complex and rganometallic Synthesis: Angelich, R., Ed.; Wiley: New York, 1989; Vol. 28, pp W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 4 th ed., Butterworth-Heinemann, xford, 1996.
3 ether, dried over anhydrous MgS 4 and purified by column chromatography (Si 2, n- hexane : ethyl acetate = 15 : 1) to afford 39.8 mg (96%) of 4-oxo-4-phenyl-butyric acid methyl ester (6a). All products were previously characterized and known compounds in literatures except 6f, 7b and 12. Ph 6a Me 4-xo-4-phenyl-butyric acid methyl ester 3 1 H NMR (250 MHz, CDCl 3 ): δ (m, 5H, Ar), 3.70 (s, 3H, Me), 3.34 (t, J = 6.6 Hz, 2H, C()CH 2 CH 2 ), 2.79 (t, J = 6.6 Hz, 2H, C()CH 2 CH 2 ). 13 C NMR (62.9 MHz, CDCl 3 ): δ198.2 (C), (C 2 ), 136.8, 133.4, 128.8, 128.2, 51.9, 33.6, MS: m/z (%): 192 (M +, 9), 161 (19), 105 (100), 77 (26). Registry Number : Me Me 6b 4-xo-4-p-tolyl-butyric acid methyl ester 4 1 H NMR (250 MHz, CDCl 3 ): δ7.89 (d, J = 8.2 Hz, 2H, Ar), 7.23 (d, J = 8.0 Hz, 2H, Ar), 3.69 (s, 3H, Me), 3.31 (t, J = 6.7 Hz, 2H, C()CH 2 CH 2 ), 2.77 (d, J = 6.7 Hz, 2H, C()CH 2 CH 2 ), 2.40 (s, 3H, CH 3 -Ar). 13 C NMR (62.9 MHz, CDCl 3 ): δ (C), (C 2 ), 144.1, 134.2, 129.4, 128.3, 51.9, 33.4, MS: m/z (%): 206 (M +, 9), 3 M. V. Bhatt, M. Ravindranathan, V. Somayaji, G. V. Rao, J. rg. Chem. 1984, 49, M. A. de las Heras, J. J. Vaquero, J. L. Garcia-Navio, J. Alvarez-Builla, Tetrahedron Letters. 1997, 38,
4 175 (17), 119 (100), 91 (21), 65 (6). Registry Number : Ph 6c t Bu 4-xo-4-phenyl-butyric acid tert-butyl ester 5 1 H NMR (250 MHz, CDCl 3 ): δ (m, 5H, Ar), 3.28 (t, J = 6.6 Hz, 2H, C()CH 2 CH 2 ), 2.70 (t, J = 6.6 Hz, 2H, (C)CH 2 CH 2 ), 1.45 (s, 9H, t Bu). MS: m/z (%): 234 (M + ), 179 (26), 161 (73), 133 (12), 105 (100), 77 (24), 57 (23), 41 (6). Registry Number : Ph 6d Et 4-xo-4-phenyl-butyric acid ethyl ester 6 1 H NMR (250 MHz, CDCl 3 ): δ (m, 5H, Ar), 4.22 (q, J = 6.2 Hz, 2H, C() 2 CH 2 CH 3 ), 3.33 (t, J = 6.6 Hz, 2H, (C)CH 2 CH 2 ), 2.77 (t, J = 6.6 Hz, 2H, C()CH 2 CH 2 ), 1.37 (t, J = 7.1 Hz, 3H, C() 2 CH 2 CH 3 ). 13 C NMR (62.9 MHz, CDCl 3 ): δ198.2 (C), (C 2 ), 136.7, 133.3, 128.7, 128.1, 60.7, 33.5, 28.4, MS: m/z (%): 206 (M +, 9), 161 (28), 105 (100), 77 (24), 51 (5). Registry Number : Me Br 6e 4-(4-Bromo-phenyl)-4-oxo-butyric acid methyl ester 3 5 M. C. Willis, S. Sapmaz, Chem. Commun. 2001, A. Arcadi, S. Cacchi, F. Marinelli, D. Misitti, Tetrahedron Letters. 1988, 29,
5 1 H NMR (250 MHz, CDCl 3 ): δ8.10 (d, J = 8.1 Hz, 2H, Ar), 7.75 (d, J = 8.1 Hz, 2H, Ar), 3.71 (s, 3H, Me), 3.36 (t, J = 6.4 Hz, 2H, C()CH 2 CH 2 ), 2.82 (t, J = 6.5 Hz, 2H, C()CH 2 CH 2 ). MS: m/z (%): 271 (M +, 1), 240 (13), 184 (100), 156 (20). Registry Number : Me F 3 C 6f 4-xo-4-(4-trifluoromethyl-phenyl)-butyric acid methyl ester 1 H NMR (250 MHz, CDCl 3 ): δ8.10 (d, J = 8.1 Hz, 2H), 7.75 (d, J = 8.1 Hz, 2H), 3.71 (s, 3H, Me), 3.36 (t, J = 6.4 Hz, 2H, C()CH 2 CH 2 ), 2.82 (t, J = 6.5 Hz, 2H, C()CH 2 CH 2 ). 13 C NMR (62.9 MHz, CDCl 3 ): δ197.4 (C), (C 2 ), 139.4, 135.0, 128.6, 126.0, 121.6, 52.1, 33.8, MS: m/z (%): 260 (M +, 6), 228 (19), 173 (100), 144 (22). IR (CDCl 3 ): 3352, 2964, 1727, 1681, 1579, 1440, 1325, 1229, 1110, 797 cm -1 ; HRMS (CI) calcd for C 12 H 12 F 3 3 ([M-H + ]) , found Anal calcd for C 12 H 11 F 3 3 : C, 55.39; H, 4.26; Found: C, 55.43; H, Me NC 6g 4-(4-Cyano-phenyl)-4-oxo-butyric acid methyl ester 3 1 H NMR (250 MHz, CDCl 3 ): δ8.09 (d, J = 8.6 Hz, 2H, Ar), 7.80 (d, J = 8.6 Hz, 2H, Ar), 3.71 (s, 3H, Me), 3.31 (t, J = 6.5 Hz, 2H, C()CH 2 CH 2 ), 2.82 (t, J = 6.5 Hz, 2H,
6 C()CH 2 CH 2 ). MS: m/z (%): 217 (M +, 6), 185 (19), 130 (100), 102 (25), 18 (12). Registry Number : NMe 2 Ph 6h N,N-Dimethyl-4-oxo-4-phenyl-butyramide 7 1 H NMR (250 MHz, CDCl 3 ): δ (m, 5H, Ar), 3.23 (t, J = 6.5 Hz, 2H, C()CH 2 CH 2 ), 2.93 (s, 3H, NMe 2 ), 2.81 (s, 3H, NMe 2 ), 2.65 (t, J = 6.4 Hz, 2H, C()CH 2 CH 2 ). MS: m/z (%): 205 (M +, 24), 161 (78), 133 (29), 105 (100), 100 (37), 77 (46), 72 (22), 51 (9), 44 (20). Registry Number : n-c 5 H 11 6i Et 4-xo-nonanoic acid ethyl ester 8 1 H NMR (250 MHz, CDCl 3 ): δ4.17 (q, J = 7.1 Hz, 2H, C() 2 CH 2 CH 3 ), 2.71 (t, J = 6.5 Hz, 2H, C()CH 2 CH 2 ), 2.59 (t, J = 6.1 Hz, 2H, C()CH 2 CH 2 ), 2.47 (t, J = 7.5 Hz, 2H, CH 2 C()), (m, 2H, CH 2 CH 2 C()), (m, 7H, CH 3 (CH 2 ) 2 (CH 2 ) 2 C(), C() 2 CH 2 CH 3 ), 0.91 (t, J = 6.6 Hz, 3H, CH 3 (CH 2 ) 4 C()). MS: m/z (%): 200 (M + ), 155 (55), 144 (84), 129 (25), 111 (16), 101 (95), 98 (100), 71 (30), 55 (18), 43 (36), 29 (13). Registry Number : J.-H. Gong, Y.-J. Im, K.-Y. Lee, J.-N. Kim, Tetrahedron Letters. 2002, 43, C. Forzato, R. Gandolfi, F. Molinari, P. Nitti, G. Pitacco, E. Valentin, Tetrahedron: Asymmetry, 2001, 12,
7 Cy 6j Et 4-Cyclohexyl-4-oxo-butyric acid ethyl ester 9 1 H NMR (250 MHz, CDCl 3 ): δ4.16 (q, J = 7.1 Hz, 2H, C() 2 CH 2 CH 3 ), 2.78 (t, J = 6.5 Hz, 2H, C()CH 2 CH 2 ), 2.59 (t, J = 6.5 Hz, 2H, C()CH 2 CH 2 ), (m, 14H, C 6 H 11 C(), C() 2 CH 2 CH 3 ). MS: m/z (%): 212 (M +, 8), 167 (39), 157 (11), 144 (10), 129 (87), 111 (33), 101 (100), 83 (87), 55 (41), 41 (15), 29 (10). Registry Number : N N H 7b t Bu (2,2-Dimethyl-propylidene)-(3-methyl-pyridin-2-yl)-amine 1 H NMR (250 MHz, CDCl 3 ): δ8.24 (d, 1H, 6-H in pyridine ring), 8.17 (s, 1H), 7.46 (d, 1H, 4-H in pyridine ring), 7.02 (t, 1H, 5-H in pyridine ring), 2.29 (s, 3H, CH 3 in pyridine ring), 1.22 (s, 9H, t-bu). 13 C NMR (62.9 MHz, CDCl 3 ): δ174.4, 160.4, 146.0, 138.2, 126.7, 120.9, 36.9, 26.7, MS: m/z (%): 176 (M +, 20), 133 (24), 119 (49), 92 (100), 65 (20). IR (CDCl 3 ): 3197, 1647, 1472, 1382, 1363, 1036, 774 cm -1 ; HRMS (CI) calcd for C 11 H 17 N 2 ([M-H + ]) , found E. Nakamura, K. Hashimoto, I. Kuwajima, J. rg. Chem. 1977, 42,
8 N N Et H 12 3-(3-Methyl-pyridin-2-ylamino)-propionic acid ethyl ester 1 H NMR (250 MHz, CDCl 3 ): δ8.02 (d, 1H, 6-H in pyridine ring), 7.22 (d, 1H, 4-H in pyridine ring), 6.54 (d, 1H, 5-H in pyridine ring), 4.23 (q, 2H, C() 2 CH 2 ), 3.81 (t, J = 6.0 Hz, 2H, NHCH 2 ), 2.69 (t, J = 6.0 Hz, 2H, NHCH 2 CH 2 ), 2.07 (s, 3H, CH 3 in pyridine ring), 1.30 (t, J = 4.3 Hz, 3H, C() 2 CH 2 CH 3 ). 13 C NMR (62.9 MHz, CDCl 3 ): δ173.2 (C 2 ), 156.3, 145.0, 136.9, 117.0, 112.6, 60.4, 37.0, 34.1, 16.8, MS: m/z (%): 208 (M +, 32), 163 (15), 135 (100), 121 (68), 108 (19), 92 (22). IR (CDCl 3 ): 3432, 2979, 1730, 1663, 1600, 1582, 1473, 1375, 1283, 1024, 773 cm -1 ; HRMS (CI) calcd for C 11 H 16 N 2 2 ([M-H + ]) , found Anal Calcd for C 11 H 17 N 2 2 : C, 63.44; H, 7.74; N, 13.45; Found: C, 63.55; H, 8.02; N, Me 6l 2-Methyl-4-oxo-4-phenyl-butyric acid methyl ester 10 1 H NMR (250 MHz, CDCl 3 ): δ (m, 5H, Ar), 3.67 (s, 3H, Me), (m, 1H, C()CH 2 CH(CH 3 )), (m, 2H, C()CH 2 CHCH 3 ), 1.33 (d, J = 8.4 Hz, 3H, C()CH 2 CH(CH 3 )). MS: m/z (%): 206 (M +, 4), 175 (11), 146 (10), 120 (11), 105 (100), 77 (24). Registry Number : B. C. Soderberg, D. C. York, E. A. Harriston, H. J. Caprara, A. H. Flurry, rganometallics. 1995, 14,
9 Me 6m 5-xo-5-phenyl-pentanoic acid methyl ester 3 1 H NMR (250 MHz, CDCl 3 ):δ (m, 5H, Ar), 3.68 (s, 3H, Me), 3.08 (t, J = 7.1 Hz, 2H, C()CH 2 CH 2 CH 2 ), 2.48 (t, J = 7.1 Hz, 2H, C()CH 2 CH 2 CH 2 ), (m, 2H, C()CH 2 CH 2 CH 2 ). 13 C NMR (62.9 MHz, CDCl 3 )δ199.5 (C), (C 2 ), 136.9, 133.2, 128.7, 128.1, 51.7, 37.6, 33.2, MS: m/z (%): 206 (M +, 7), 175 (14), 147 (10), 120 (19), 105 (100), 77 (31). Registry Number : Me 6o 6-xo-6-phenyl-hexanoic acid methyl ester 3 1 H NMR (250 MHz, CDCl 3 ):δ (m, 5H, Ar), 3.67 (s, 3H, Me), 3.03 (t, J = 6.9 Hz, 2H, C()CH 2 (CH 2 ) 2 CH 2 ), 2.41 (t, J = 6.9 Hz, 2H, C()(CH 2 ) 3 CH 2 ), (m, 4H, C()CH 2 (CH 2 ) 2 CH 2 ). MS: m/z (%): 220 (M + ), 143 (14), 120 (49), 105 (100), 77 (28). Registry Number :
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