Asymmetric Synthesis of Substituted Prolines from δ-Amino β-Ketoesters. Methyl (2S,5R)-(+)-5-Phenylpyrrolidine-2-carboxylate

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1599-1602

  Davis, Franklin A ^a   Fang, Tianan ^a   Goswami, Rajesh ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLECYSTOKININ; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OXOACID; PIPERIDINE DERIVATIVE; PROLINE; SS 20846A;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

CHOLECYSTOKININ; INDICATORS AND REAGENTS; KETO ACIDS; PIPERIDINES; PROLINE; STEREOISOMERISM;

EID: 0037007709     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025831j     Document Type: Article

References (18)

1. Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041.
2. Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623.
3. Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106.
4. Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
5. (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis, with Diazo Compounds, Wiley-Interscience: New York, 1998.
6. (b) Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983.
7. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
8. Wang, J.; Hou, Y.; Wu, P. J. Chem. Soc., Perkin Trans. 1 1999, 2277.
9. Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161.
10. Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223.
11. Yang, H.; Jurkauskas, V.; Mackintosh, N.; Mogren, T.; Stephenson, C. R. J.; Foster, K.; Brown, W.; Roberts, E. Can. J. Chem. 2000, 78, 800.
12. Garcia, C. F.; McKervey, M. A.; Ye, T. Chem. Commun. 1996, 1565.
13. For examples of carbenoid insertion into the N - H bond of a sulfonamide, see: (a) Benati, L.; Calestani, G.; Nanni, D.; Spagnolo, P. J. Org. Chem. 1998, 63, 4679. See also ref 215 in ret 5c.
14. Manfre, F.; Pulicani, J. P. Tetrahedron: Asymmetry 1994, 5, 235.
15. Haddad, M.; Imogai, H.; Larcheveque, M. J. Org. Chem. 1998, 63, 5680.
16. McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
17. (a) Comins, D. L.; LaMunyon, D, H.; Chen, X. J. Org. Chem. 1997, 62, 8182.
18. (b) Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794.