Enantioselective synthesis of 4-substituted 2-pyrrolidinones by site- selective C-H insertion of α-methoxycarbonyl-α-diazoacetanilides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 79-82

  Anada, Masahiro ^a   Hashimoto, Shun Ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDINONE; ACETANILIDE DERIVATIVE; BACLOFEN; CARBONYL DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0031983769     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10493-2     Document Type: Article

References (35)

1. For reviews, see: (a) Ye, T.; McKervey, M.A. Chem. Rev. 1994, 94, 1091.
2. (b) Doyle, M.P. Aldrichim. Acta 1996, 29, 3.
3. (c) Doyle, M.P.; McKervey, M.A. Chem. Commun. 1997, 983.
4. (a) Hashimoto, S.; Watanabe, N.; Sato, T.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1993, 34, 5109.
5. (b) Hashimoto, S.; Watanabe, N.; Ikegami, S. Synlett 1994, 353.
6. (a) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
7. (b) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85.
8. Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031.
9. (a) Doyle, M.P.; Shanklin, M.S.; Oon, S.; Pho, H.Q.; van der Heide, F.R.; Veal, W.R. J. Org. Chem. 1988, 53, 3384.
10. (b) Doyle, M.P.; Taunton, J.; Pho. H.Q. Tetrahedron Lett. 1989, 30, 5397.
11. Wee A.G.H., Liu B., Zhang L. J. Org. Chem. 57:1992;4404.
12. Doyle M.P., Protopopova M.N., Winchester W.R., Daniel K.L. Tetrahedron Lett. 33:1992;7819.
13. Wee A.G.H., Liu B. Tetrahedron Lett. 37:1996;145.
14. No trace of 3,4-cis isomer could be detected.
15. Doyle M.P., Shanklin M.S., Pho H.Q., Mahapatro S.N. J. Org. Chem. 53:1988;1017.
16. Cox G.G., Moody C.J., Austin D.J., Padwa A. Tetrahedron. 49:1993;5109.
17. Padwa A., Austin D.J., Price A.T., Semones M.A., Doyle M.P., Protopopova M.N., Winchester W.R., Tran A. J. Am. Chem. Soc. 115:1993;8669.
18. 2 was used for further exploration.
19. Owsley, D.C.; Bloomfield, J.J. Synthesis 1977, 118.
20. Fukase K., Yasukochi T., Nakai Y., Kusumoto S. Tetrahedron Lett. 37:1996;3343.
21. Zelle, R.E. Synthesis 1991, 1023.
22. Davies H.M.L., Bruzinski P.R., Lake D.H., Kong N., Fall M.J. J. Am. Chem. Soc. 118:1996;6897.
23. 4 occurred in 1,2-dichloroethane under reflux to give a complex mixture of products.
24. Langlois N., Dahuron N. Tetrahedron Lett. 37:1996;3993.
25. Kerr D.I.B., Ong J. Med. Res. Rev. 12:1992;593.
26. (a) Chênevert, R.; Desjardins, M. Tetrahedron Lett. 1991, 32, 4249.
27. (b) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312.
28. (c) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195.
29. (a) Herdeis, C.; Hubmann, H.P. Tetrahedron: Asymmetry 1992, 3, 1213.
30. (b) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63.
31. (c) Yoshifuji, s.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302.
32. (d) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117.
33. Lantz, R.L.; Obellianne, P. Bull. Soc. Chim. Fr. 1956, 311.
34. Olpe H.-R., Demiéville H., Baltzer V., Bencze W.L., Koella W.P., Wolf P., Haas H.L. Eur. J. Pharmacol. 52:1978;133.
35. This research was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Science, Sports and Culture, Japan and also by the Special Coordination Funds of the Science and Technology Agency of the Japanese Government. The authors thank the Japan Society for the Promotion of Science for Research Fellowships for Young Scientists (to M.A.).