Asymmetric reduction of 2-(N-arylimino)-3,3,3-trifluoropropanoic acid esters leading to enantiomerically enriched 3,3,3-trifluoroalanine

Tetrahedron

Volumn 52, Issue 1, 1996, Pages 233-244

  Sakai, Takashi ^a   Yan, Fengyang ^a   Kashino, Setsuo ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3,3,3 TRIFLUOROALANINE; ALANINE DERIVATIVE; UNCLASSIFIED DRUG;

CHIRALITY; CONFERENCE PAPER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0029656035     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00866-7     Document Type: Article

References (50)

1. Faraci, W. S.; Walsh, C. T. Biochemistry 1989, 28, 431.
2. (a) Welch, J. T.; Eswarakrishnan, S. "Fluorine in Bioorganic Chemistry" John Wiley & Sons, New York 1991.
3. (b) Bravo, P.; Capelli, S.; Meille, S. V.; Viani, F.; Zanda, M.; Kukhar, V. P.; Soloshonok, V. A. Tetrahedron Asymm. 1994, 5, 2009.
4. (a) Weygand, F.; Steglich, W.; Fraunberger, F. Angew. Chem., Int. Ed. Engl. 1967, 6, 808.
5. (b) Weygand, F.; Steglich, W.; Oettmei, W. Chem. Ber. 1970, 103, 818.
6. (c) Burger, K.; Hubl, D.; Gertitschke, P. J. Fluorine Chem. 1985, 27, 327.
7. (d) Hofle, K.; Steiglich, W. Chem. Ber. 1971, 104, 1408.
8. (e) Kukhar, V. P.; Soloshonok, V. A. Eds., "Fluorine-Containing Amino Acids: Synthesis and Properties" John Wiley & Sons, Chichester 1995.
9. Kubota, T.; Masaki, F.; Katagiri, T. Japan Kokai, JP 5-186411 (1993).
10. Kukhar, V. P. J. Fluorine Chem. 1994, 69, 199.
11. (a) Tamura, K.; Mizukami, H.; Maeda, K.; Watanabe, H.; Uneyama, K. J. Org. Chem. 1993, 58, 32.
12. (b) Watanabe, H.; Hashizume, Y.; Uneyama, K. TetrahedronLett. 1992, 33, 4333.
13. (a) Bolm, C. Angew. Chem. 1990, 102, 561.
14. (b) Bolm, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 232.
15. (a) Enantioselectivity was up to 91% ee in the hydrogenation of N-benzylimino of p-methoxyacetophenone with rhodium complex: Kang, G.-J.; Cullen, W. R.; Fryzuk, M. D.; James, B. R.; Kuteny, J. P. J. Chem. Soc., Chem. Commun. 1988, 1466.
16. (b) Asymmetric rediction of N-acylhydrazones with DuPHOS-Rh catalyst (99% ee best): Burk, M. J.; Martinez, J. P.; Feaster, J. E.; Cosford, N. Tetrahedron 1994, 50, 4399.
17. (c) Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
18. (d) Lensink, C.; de Vries, J. G. Tetrahedron Asymm. 1993, 4, 215.
19. (e) Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sinou, D. J. Chem. Soc., Chem. Commun. 1991, 1684.
20. For cyclic imines (80% ee best): (a) Ng Cheong Chan, Y.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400.
21. (b) Spindler, F.; Pugin, B.; Blaser, H.-U. Angew. Chem. Int. Ed. Engl. 1990, 29, 558.
22. For cyclic imines (99% ee best): (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1992, 114, 7562.
23. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
24. (c) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703.
25. (a) Wallbaum, S.; Martens, J. Tetrahedron Asymm. 1992, 3, 1475.
26. (b) Cho, B. T.; Chun, Y. S. Tetrahedron Asymm. 1992, 3, 337.
27. (c) Cho, B. T.; Chun, Y. S. J. Chem. Soc., Perkin Trans. I 1990, 3200.
28. (d) Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Perkin Trans. I 1985, 2039.
29. (e) Itsuno, S.; Nakano, M.; Ito, K.; Hirao, A.; Owa, M.; Kanda, N.; Nakahama, S. J. Chem. Soc. Perkin Trans. I 1985, 2615.
30. Kawate, T.; Nakagawa, M.; Hino, T. Tetrahedron Asymm. 1992, 3, 227.
31. (a) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
32. (b) Itsuno, S.; Sakurai, Y.; Shimizu, K.; Ito, K. J. Chem. Soc., Perkin Trans. I 1989, 1548.
33. (c) Itsuno, S.; Sakurai, Y.; Shimizu, K.; Ito, K. J. Chem. Soc., Perkin Trans. I 1990, 1859.
34. Bolm, C.; Eelder, M. Synlett 1994, 655.
35. Sakai, T.; Yan, F.-Y.; Uneyama, K. Synlett 1995, 753.
36. (a) Corey, E. J.; Bakshi, R. K.; Shibita, S. J. Am. Chem. Soc. 1987, 109, 5551.
37. (b) Corey, E. J.; Bakshi, R. K.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
38. (a)) Corey, E. J.; Link, J. O.; Bakshi, R. Tetrahedron Lett. 1992, 33, 7107.
39. (b) Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431.
40. (c) Corey, E. J.; Bakshi, R. K. TetrahedronLett. 1990, 31, 611.
41. (a) Martens, J.; Dauelsberg, C.; Behnen, W.; Wallbaum, S. Tetrahedron Asymm. 1992, 3, 347.
42. (b) Youn, I. K.; Lee, S. W.; Pak, C. S. Tetrahedron Lett. 1988, 29, 4453.
43. Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones E. T. E.; Reimer, R. A.; Roberts, F. E.; Grabowaki, E. J. J. J. Org. Chem. 1991, 56, 763.
44. 3).
45. Jacob, P.; Callery, P. S.; Shulgin, A. T.; Castagnoli, N. J. Org. Chem. 1976, 41, 3627.
46. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem . 1969, 34, 1548.
47. (a) Grochowski, E.; Jurczak, J. Synthesis 1976, 682.
48. (b) Welch, J. T.; Seper, K. W. J. Org. Chem. 1988, 53, 2991.
49. (c) Kawate, T.; Nakagawa, M.; Hino, T. Tetrahedron Asymm. 1992, 3, 227.
50. 3 was prepared by the known method: Ukai, T.; Kawazura, Y.; Ishii, Y. J. Organomet. Chem. 1974, 65, 253.