Synthesis of optically active α-amino esters via dynamic kinetic resolution: A mechanistic study

Journal of Organic Chemistry

Volumn 64, Issue 21, 1999, Pages 7700-7706

  Ben, Robert ^a   Durst, Tony ^b  

^a BINGHAMTON UNIVERSITY   (United States)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; BINDING KINETICS; MOLECULAR DYNAMICS; ORGANIC CHEMISTRY; RACEMIC MIXTURE; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032722407     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9811625     Document Type: Article

References (24)

1. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
2. Meijer, E. M.; Boestan, W. H. J.; Schoemaker, H. E.; Van Blaken, J. A. M. In Biocatalysis in Organic Synthesis; Tramper, J., Van der Plas, H. C., Linko, P., Eds.; Elsevier Publishing: Amsterdam, 1985; p 135.
3. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
4. Sheih, W-C; Carlson, J. A.; Zaunius, G. M. J. Org. Chem. 1997, 62, 8271.
5. Koh, K.; Ben, R. N.; Durst, T. Tetrahedron Lett. 1993, 34, 4473.
6. Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799.
7. It has been proposed that the oxygen of the lactone carbonyl may participate in displacement of the bromide. The resulting bicyclic oxonium ion could then undergo reaction with benzylamine to furnish products 2 and 3. This reaction pathway is not likely since diastereomerically enriched mixtures of products would not be expected or obtained.
8. Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. Kubota, H.; Kubo, A.; Nunami, K. Tetrahedron Lett. 1994, 35, 3107. Nunami, K.; Kubota, H.; Kubo, A. Tetrahedron Lett. 1994, 35, 8639. Kubota, H.; Kubo, A.; Takahashi, M.; Shimizu, R.; Date, T.; Okamura, K.; Nunami, K. J. Org. Chem. 1995, 60, 6776.
9. Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. Kubota, H.; Kubo, A.; Nunami, K. Tetrahedron Lett. 1994, 35, 3107. Nunami, K.; Kubota, H.; Kubo, A. Tetrahedron Lett. 1994, 35, 8639. Kubota, H.; Kubo, A.; Takahashi, M.; Shimizu, R.; Date, T.; Okamura, K.; Nunami, K. J. Org. Chem. 1995, 60, 6776.
10. Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. Kubota, H.; Kubo, A.; Nunami, K. Tetrahedron Lett. 1994, 35, 3107. Nunami, K.; Kubota, H.; Kubo, A. Tetrahedron Lett. 1994, 35, 8639. Kubota, H.; Kubo, A.; Takahashi, M.; Shimizu, R.; Date, T.; Okamura, K.; Nunami, K. J. Org. Chem. 1995, 60, 6776.
11. Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. Kubota, H.; Kubo, A.; Nunami, K. Tetrahedron Lett. 1994, 35, 3107. Nunami, K.; Kubota, H.; Kubo, A. Tetrahedron Lett. 1994, 35, 8639. Kubota, H.; Kubo, A.; Takahashi, M.; Shimizu, R.; Date, T.; Okamura, K.; Nunami, K. J. Org. Chem. 1995, 60, 6776.
12. Larsen, R. D.; Corley, E. G.; Davis, P.; Reider, P. J.; Grabowski, E. J. J. Am. Chem. Soc. 1989, 111, 7650.
13. Davies, H. M. L.; Cantrell, W. R. Tetrahedron Lett. 1991, 32, 6509.
14. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095.
15. Ben, R. N.; Durst, T. Unpublished results.
16. Loncharich, R. T.; Schwartz, T. R.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 14. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
17. Loncharich, R. T.; Schwartz, T. R.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 14. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
18. Streitwieser, A. Solvolytic Displacement Reactions; McGraw-Hill Book Company Inc.: New York, 1962; p 26.
19. Allinger, K. B.; Kuchsiang, C.; Rahman, M.; Pathiaseril, A. J. Am. Chem. Soc. 1991, 113, 4505.
20. Koh, K.; Durst, T. J. Org. Chem. 1994, 59, 4683.
21. Koh, K.; Durst, T. Unpublished results.
22. O'Meara, J. A.; Gardee, N.; Jung, M.; Ben, R. N.; Durst, T. J. Org. Chem. 1998, 63, 3117. Koh, K.; Ben, R. N.; Durst, T. Tetrahedron Lett. 1994, 35, 375.
23. O'Meara, J. A.; Gardee, N.; Jung, M.; Ben, R. N.; Durst, T. J. Org. Chem. 1998, 63, 3117. Koh, K.; Ben, R. N.; Durst, T. Tetrahedron Lett. 1994, 35, 375.
24. Harpp, D. W.; Black, C. J:; Gleason, J. G.; Smith, R. A. J. Org. Chem. 1975, 40, 3420.