Solvent-free synthesis of β-hydroxy esters and β-amino esters by indium-mediated reformatsky reaction

Synthesis

Volumn , Issue 20, 2007, Pages 3233-3239

  Chen, Xi'an ^a   Zhang, Changfu ^a,b   Wu, Huayue ^a   Yu, Xiaochun ^a   Su, Weike ^a,c   Cheng, Jiang ^a  

^a WENZHOU UNIVERSITY   (China)

^b GUIZHOU UNIVERSITY   (China)

^c ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

amino esters; hydroxy esters; Indium; Reformatsky reaction; Solvent free

Indexed keywords

ALDIMINES; AMINO ESTERS; REFORMATSKY REACTION;

ALDEHYDES; INDIUM; ORGANIC SOLVENTS; REACTION KINETICS;

ESTERS;

BETA AMINO ESTER DERIVATIVE; BETA HYDROXY ESTER DERIVATIVE; DIETHYL 3,3' (1,4 PHENYLENE)BIS(3 HYDROXYPROPANOATE); ESTER DERIVATIVE; ETHYL 3 (1,3 BENZODIOXOL 5 YL) 3 HYDROXYPROPANOATE; ETHYL 3 (2 FURYL) 3 HYDROXYPROPANOATE; ETHYL 3 (2 METHOXYANILINO) 3 3 TOLYLPROPANOATE; ETHYL 3 (2 METHOXYANILINO) 3 PHENYLPROPANOATE; ETHYL 3 (3 BROMOPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 (3 TOLUIDINO) 3 3 TOLYLPROPANOATE; ETHYL 3 (4 BROMOPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 (4 CHLOROANILINO) 3 3 TOLYLPROPANOATE; ETHYL 3 (4 CHLOROANILINO) 3 PHENYLPROPANOATE; ETHYL 3 (4 CHLOROPHENYL) 3 HYDROXY 2 METHYLPROPANOATE; ETHYL 3 (4 CHLOROPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 (4 FLUOROPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 (4 FORMYLPHENYL) 3 HYDROXYPROPANOATE; ETHYL 3 ANILINO 2 METHYL 3 PHENYLPROPANOATE; ETHYL 3 ANILINO 3 (4 CHLOROPHENYL)PROPANOATE; ETHYL 3 ANILINO 3 3 TOLYLPROPANOATE; ETHYL 3 ANILINO 3 PHENYLPROPANOATE; ETHYL 3 HYDROXY 2 METHYL 3 3 TOLYLPROPANOATE; ETHYL 3 HYDROXY 2 METHYL 3 PHENYLPROPANOATE; ETHYL 3 HYDROXY 3 (2 HYDROXYPHENYL)PROPANOATE; ETHYL 3 HYDROXY 3 (4 METHOXYPHENYL)PROPANOATE; ETHYL 3 HYDROXY 3 3 TOLYLPROPANOATE; ETHYL 3 HYDROXY 3 PHENYLPROPANOATE; ETHYL 3 HYDROXY 5 PHENYLPENT 4 ENOATE; ETHYL 3 HYDROXY 5 PHENYLPENTANOATE; INDIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REFORMATSKY REACTION; SYNTHESIS;

EID: 35548982108     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990799     Document Type: Article

References (58)

1. (a) Gensler, W. J. Chem. Rev. 1957, 57, 265.
2. (b) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89.
3. (c) Fürstner, A. Synthesis 1989, 571.
4. (d) Ocampo, R.; Dolbier, W. R. Tetrahedron 2004, 60, 9325.
5. (e) Orsini, F.; Sello, G. Curr. Org. Synth. 2004, 1, 111.
6. (a) Becker, D.; Brodsky, N.; Kalo, I. J. Org. Chem. 1978, 43, 2557.
7. (b) Barco, A.; Benett, S.; Pollini, G. P. J. Org. Chem. 1980, 45, 4776.
8. (c) Klipa, D. K.; Hart, H. J. Org. Chem. 1981, 46, 2815.
9. (d) West, F. G.; Gunawardena, G. V. J. Org. Chem. 1993, 58, 5043.
10. (e) Witzemann, J. S.; Nottingham, W. D. J. Org. Chem. 1989, 54, 3258; and references cited therein.
11. Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
12. Santaniello, E.; Manzocchi, A. Synthesis 1977, 698.
13. Csuk, R.; Fürstner, A.; Weidmann, H. J. Chem. Soc., Chem. Commun. 1986, 775.
14. (a) Moriwake, T. J. Org. Chem. 1996, 31, 983.
15. (b) Borno, A.; Bigley, D. B. J. Chem. Soc., Perkin Trans. 2 1983, 1311.
16. Burkhardt, E.; Rieke, R. D. J. Org. Chem. 1985, 50, 416.
17. Inaba, S.-I.; Rieke, R. D. Tetrahedron Lett. 1985, 26, 155.
18. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
19. Villieras, J.; Perriot, P.; Bourgain, M.; Normant, J. F. J. Organomet. Chem. 1975, 102, 129.
20. Wessjohann, L.; Wild, H. Synlett 1997, 731.
21. Orsini, F.; Lucci, E. M. Tetrahedron Lett. 2005, 46, 1909.
22. Suh, Y. S.; Rieke, R. D. Tetrahedron Lett. 2004, 45, 1807.
23. Kanai, K.; Wakabayashi, H.; Honda, T. Org. Lett. 2000, 2, 2549.
24. Durandetti, M.; Périchon, J. Synthesis 2006, 1542.
25. (a) Nari, V.; Ros, S.; Jayan, C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959.
26. (b) Podlech, J.; Maier, T. Synthesis 2003, 633.
27. (c) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
28. (d) Li, C. J. Tetrahedron 1996, 52, 5643.
29. (e) Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 48, 7071.
30. (f) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
31. (a) Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253.
32. (b) Ariak, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453.
33. (c) Bang, K.; Lee, K.; Park, Y. K.; Lee, P. H. Bull. Korean Chem. Soc. 2002, 23, 1272.
34. (d) Srinivasarao, A. B.; Makoto, Y.; Ikuya, S.; Akio, B. J. Org. Chem. 2005, 70, 10408.
35. (a) Murahashi, S. I.; Kodera, Y.; Hosomi, T. Tetrahedron Lett. 1988, 29, 5949.
36. (b) Ogumi, N.; Omi, T.; Yamamoto, Y.; Nakamura, A. Chem. Lett. 1983, 841.
37. (c) Saidi, M. R.; Azizi, N.; Boinee, H. Z. Tetrahedron 2001, 57, 6829.
38. For a review of the Reformatsky reaction, see ref. 1c.
39. (a) Mohan, S.; Sethi, P. S.; Kapoor, A. L. J. Indian Chem. Soc. 1971, 48, 685.
40. (b) Dardoize, F.; Moreau, J. L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1972, 3841.
41. (c) Chen, L.; Zhao, G.; Ding, Y. Tetrahedron Lett. 2003, 44, 2611.
42. (d) Banik, B. K.; Ghatak, A.; Becker, F. F. J. Chem. Soc., Perkin Trans. 1 2000, 2179.
43. (e) Ross, N. A.; Macgregor, R. R.; Bartsch, R. A. Tetrahedron 2004, 60, 2035.
44. (a) Adrian, J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457.
45. (b) Adrian, J. C.; Snapper, M. L. J. Org. Chem. 2003, 68, 2143.
46. (a) Su, W. K.; Chen, J. X.; Wu, H. Y.; Jin, C. J. Org. Chem. 2007, 72, 4524.
47. (b) Chen, J. X.; Wu, H. Y.; Zheng, Z. G.; Jin, C.; Zhang, X. X.; Su, W. K. Tetrahedron Lett. 2006, 47, 5383.
48. (c) Chen, J. X.; Wu, H. Y.; Jin, C.; Zhang, X. X.; Xie, Y. Y.; Su, W. K. Green Chem. 2006, 8, 330.
49. (d) Wu, H. Y.; Ding, J. C.; Gao, J.; Liu, M. C. J. Chem. Res., Synop. 2003, 724.
50. (e) Wu, H. Y.; Ding, J. C. J. Chem. Res., Synop. 2002, 461.
51. (a) Tanaka, K.; Kishigami, S.; Toda, F. J. Org. Chem. 1991, 56, 4333.
52. (b) Gholap, A. R.; Chavan, A. P. J. Chem. Res., Synop. 2003, 6, 374.
53. Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691.
54. Wan, X.; Sun, Y.; Luo, Y.; Li, D.; Zhang, Z. J. Org. Chem. 2005, 70, 1070.
55. Robert, J. M.; Norman, H. C. J. Org. Chem. 1976, 41, 3540.
56. Shibata, I.; Suwa, T.; Ryu, K.; Baba, A. J. Org. Chem. 2001, 66, 8690.
57. Komoto, I.; Kobayashi, S. Org. Lett. 2002, 4, 1115.
58. Tanaka, N.; Masaki, Y. Synlett 2000, 406.