Catalytic diastereoselective Pauson-Khand reaction: An efficient route to enantiopure cyclopenta[c]proline derivatives

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4077-4080

  Jiang, Biao ^a   Xu, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; PROLINE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; PEPTIDES, CYCLIC; PROLINE; STEREOISOMERISM;

EID: 0037078850     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026826i     Document Type: Article

References (27)

1. (a) Ager, D. J.; Fotheringham, I. G. Curr. Opin. Drug Discovery Dev. 2001, 4, 800.
2. (b) Petersen, M.; Sauter, M. Chimia 1999, 53, 608.
3. (a) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535.
4. (b) Mourabit A. A.; Potier, P. Eur. J. Org. Chem. 2001, 237.
5. (c) Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159.
6. (d) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793.
7. (a) Kopach, M. E.; Fray, A. H.; Meyers, A. I. J. Am. Chem. Soc. 1996, 118, 9876.
8. (b) Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Itô, S. Tetrahedron Lett. 1996, 37, 2463.
9. For recent reviews on the Pauson-Khand reaction, see: (a) Brummend, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
10. (b) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657.
11. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297,
12. (d) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911.
13. (a) Alcarde, B.; Planco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786.
14. (b) Mukai, C.; Kim, J. S.; Sonobe, H.; Hanaoka, M. J. Org. Chem. 1999, 64, 6822.
15. (c) Carretero, J. C.; Adrio, J. J. Am. Chem. Soc. 1999, 121, 7411.
16. (d) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947.
17. (a) Petasis, N. A.; Goodman, A.; Zavialov, I. A. Tetrahedron 1997, 53, 16463.
18. (b) Petasis, N. A.; Goodman, A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
19. Jiang, B.; Yang, C.-G.; Gu, X.-H. Tetrahedron Lett. 2001, 42, 2545.
20. For the first report of an intramolecular Pauson-Khand reaction, see: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
21. Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
22. Pagenkopf, B. C.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
23. (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
24. (b) Rautenstrauch, V.; Megard, P.; Conesa, J.; Kuster, W. Angew. Chem., Int. Ed. 1990, 29, 1413.
25. Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. Tetrahedron Lett 1999, 40, 9171.
26. Hayashi, M.; Hashimoto, Y.; Yamamoto, Y.; Usuki, J.; Saigo, K. Angew. Chem., Int. Ed. 2000, 39, 631.
27. Adrio, J.; Rivero, M. R.; Carretero, J. C. Chem. Eur. J. 2001, 7, 2435.