Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6264-6267

  Li, Bin Feng ^a   Yuan, Ke ^a   Zhang, Ming Jie ^a   Wu, Hao ^b   Dai, Li Xin ^a   Wang, Quan Rui ^b   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DERIVATIVES; STEREOCHEMISTRY;

DIASTEREOSELECTIVITY;

AMINES;

ALDEHYDE; ALIPHATIC COMPOUND; AZIRIDINE DERIVATIVE; CESIUM; DIAMINO ACID; FLUORIDE; HYDROGEN; IMINE; NITRILE; SULFINIMINE; THIOPHENOL; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; RING OPENING; STEREOCHEMISTRY; STRECKER SYNTHESIS;

EID: 0043032834     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034477f     Document Type: Article

References (44)

1. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, UK, 1989.
2. Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
3. For representative recent examples, see: (a) Duthaler, O. R. Tetrahedron 1994, 50, 1539. (b) Kunz, H.; Rick, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. (c) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (d) Meyers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656.
4. For representative recent examples, see: (a) Duthaler, O. R. Tetrahedron 1994, 50, 1539. (b) Kunz, H.; Rick, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. (c) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (d) Meyers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656.
5. For representative recent examples, see: (a) Duthaler, O. R. Tetrahedron 1994, 50, 1539. (b) Kunz, H.; Rick, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. (c) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (d) Meyers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656.
6. For representative recent examples, see: (a) Duthaler, O. R. Tetrahedron 1994, 50, 1539. (b) Kunz, H.; Rick, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. (c) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (d) Meyers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656.
7. (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
8. (b) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284.
9. (c) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910.
10. (d) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
11. (e) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762.
12. (a) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410.
13. (b) Davis, F. A.; Mohanty, P. K. J. Org. Chem. 2002, 67, 1290.
14. (c) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
15. (d) Davis, F. A.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13.
16. (e) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127.
17. (f) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772.
18. (g) Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. D.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
19. (h) Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011.
20. (i) Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532.
21. Davis, F. A.; Reddy, R. E.; Portonovo, P. Tetrahedron Lett. 1994, 35, 9351.
22. (a) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. H. J. Org. Chem. 1996, 61, 440.
23. (b) Davis, F. A.; Fanelli, K. L. J. Org. Chem. 1998, 63, 1981.
24. (c) Davis, F. A.; Srirajan, V.; Titus, D. D. J. Org. Chem. 1999, 64, 6931.
25. (d) Davis, F. A.; Srirajan, V. J. Org. Chem. 2000, 65, 3248.
26. (e) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663.
27. (f) Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 65, 8704.
28. (a) Wang, D. K.; Zhou, Y. G.; Tang, Y.; Hou, X. L.; Dai, L. X. J. Org. Chem. 1999, 64, 4233.
29. (b) Li, A. H.; Dai, L. X.; Hou, X. L. Chem. Commun. 1996, 491.
30. (c) Wang, D. K.; Dai, L. X.; Hou, X. L. Chem. Commun. 1997, 1231.
31. (d) Hou, X. L.; Yang, X. F.; Dai, L. X.; Chen, X. F. Chem. Commun. 1998, 747.
32. (e) Hou, X. L.; Zheng, X. L.; Dai, L. X. Tetrahedron Lett. 1998, 39, 6949.
33. (f) Li, B. F.; Zhang, M. J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2002, 67, 2902.
34. (g) Yang, X. F.; Zhang, M. J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2002, 67, 8097.
35. (a) Wu, J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2000, 65, 1344.
36. (b) Wu, J.; Hou, X. L.; Dai, L. X. J. Chem. Soc., Perkin Trans. 1 2001, 1314.
37. (c) Hou, X. L.; Fan, R. H.; Dai, L. X. J. Org. Chem. 2002, 67, 5295.
38. (d) Fan, R. H.; Hou, X. L. J. Org. Chem. 2003, 68, 726.
39. (e0 Fan, R. H.; Hou, X. L. Org. Biomol. Chem. 2003, 1, 1565.
40. (a) DeWitt, H. D.; Ingersoll, A. W. J. Am. Chem. Soc. 1951, 73, 3359.
41. (b) Wang, M X.; Lin, S. J. J. Org. Chem. 2002, 67, 6542.
42. (c) Reference 7f and references therein.
43. For example, see: Luo, Y.; Blaskovich, M. A.; Lajoie, G. A. J. Org. Chem. 1999, 64, 6106 and references therein.
44. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.