Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5147-5152

  Davis, Franklin A ^a   Yang, Bin ^a   Deng, Jianghe ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INSERTION REACTIONS;

REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ESTERS;

5 TERT BUTYLPROLINE; CARBENOID; DELTA AMINO ALPHA DIAZOESTER; ESTER DERIVATIVE; HYDROGEN; METAL; NITROGEN; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; STEREOCHEMISTRY; SYNTHESIS;

AMINES; CATALYSIS; CHEMISTRY, ORGANIC; ESTERS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PROLINE; RHODIUM; STEREOISOMERISM;

EID: 0038209587     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030081s     Document Type: Article

References (26)

1. Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599.
2. For references to the application of N-sulfinyl α-amino β-keto esters for the asymmetric synthesis of piperidine derivatives see: (a) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
3. For references to the application of N-sulfinyl α-amino β-keto esters for the asymmetric synthesis of piperidine derivatives see: (a) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
4. For references to the application of N-sulfinyl α-amino β-keto esters for the asymmetric synthesis of piperidine derivatives see: (a) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
5. For references to the application of N-sulfinyl α-amino β-keto esters for the asymmetric synthesis of piperidine derivatives see: (a) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
6. Beausoleil, E.; L'Archeveque, B.; Belec, L.; Atfani, M.; Lubell, W. D. J. Org. Chem. 1996, 61, 9447.
7. Halab, L.; Belec, L.; Lubell, W. D. Tetrahedron 2001, 57, 6439.
8. Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
9. 3OD these carbons were easily observable. We speculate that hydrogen bonding, i and ii, may be responsible for broadening the signals of these carbons in the former solvent.
10. Deng, G.; Jiang, N.; Ma, Z.; Wang, J. Synlett 2002, 1913.
11. Danheiser, R. F.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959.
12. (a) Doyle, M. P. Chem. Rev. 1986, 86, 919.
13. (b) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 4.2.
14. (c) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2.
15. (d) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
16. (e) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1998.
17. For an excellent review of the relevant literature see: Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc. 2002, 124, 7181.
18. Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196.
19. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958.
20. (a) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547.
21. (b) Taber, D. F.; Malcolm, S. C. J. Org. Chem. 1998, 63, 3717.
22. See ref 9e, Chapter 8.
23. Helson, H. E.; Jorgensen, W. L. J. Org. Chem. 1994, 59, 3841.
24. (a) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161.
25. (b) Ratcliffe, R. W.; Salzmann, T. N.; Christensen, B. G. Tetrahedron Lett. 1980, 21, 31.
26. Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. P. J. Org. Chem. 1996, 61, 440.