Stereocontrol by Lewis acids in the hetero-diels-alder reaction leading to a key 1β-methylcarbapenem intermediate

Chemistry Letters

Volumn , Issue 4, 1996, Pages 321-322

  Nishiuchi, Masaki ^a   Honda, Keisuke ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004956974     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.321     Document Type: Article

References (10)

1. D. H. Shih, F. Backer, L. Cama, and B. G. Christensen, Heterocycles, 21, 29 (1984).
2. For a pertinent list of references, see: N. Tsukada, T. Shimada, Y. S. Gyoung, N. Asao, and Y. Yamamoto, J. Org. Chem., 60, 143 (1995);
3. H. Itani and S. Uyeo, Synlett, 1995, 213;
4. H. Ishibashi, K. Kodama, C. Kameoka, H. Kawanami, and M. Ikeda, Synlett, 1995, 912;
5. H. Ishibashi, C. Kameoka, K. Kodama, and M. Ikeda, Synlett, 1995, 915;
6. T. Fujisawa. R. Hayakawa, and M. Shimizu, Chem. Lett., 1995, 1013; and references cited therein.
7. a) R. Bayles, A. P. Flynm, R. H. B. Gait, S. Kirby, and R. W. Turner, Tetrahedron Lett., 29, 6341 (1988);
8. b) R. Bayles, A. P. Flynm, R. H. B. Galt, S. Kirby, and R. W. Turner, Tetrahedron Lett., 29, 6345 (1988);
9. ) R. Bayles, A. P. Flynm, and R. W. Turner, European Patent EP, 230, 771 (1991).
10. In our hands, the thermal reaction in toluene at -30 °C gave a 46:54 mixture of cis- and trans-4.