Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications

Journal of the American Chemical Society

Volumn 120, Issue 46, 1998, Pages 11943-11952

  Charette, André B ^a   Juteau, Hélène ^a   Lebel, Hélène ^a   Molinaro, Carmela ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER;

EID: 0032567221     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982055v     Document Type: Article

References (9)

1. For interesting examples of natural and unnatural products containing a chiral, nonracemic cyclopropane, see the folowing: (a) FR-900848: Yoshida, M.; Ezaki, M.; Hashimoto, M.; Yamashita, M.; Shigematsu, N.; Okuhara, M.; Kohsaka, M.; Horikoshi, K. J. Antibiot. 1990, 43, 748-754.
2. (b) U-106305: Kuo, M. S.; Zielinski, R. J.; Cialdella, J. I.; Marschke, C. K.; Dupuis, M. J.; Li, G. P.; Kloosterman, D. A.; Spilman, C. H.; Marshall, V. P. J. Am. Chem. Soc. 1995, 117, 10629-10634.
3. (c) Callipeltoside A: Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085-11088.
4. (d) Aragusterol A: Iguchi, K.; Shimura, H.; Taira, S.; Yokoo, C.; Matsumoto, K.; Yamada, Y. J. Org. Chem. 1994, 59, 7499-7502.
5. (e) Curacin A: Nagle, D. G.; Geralds, R. S.; Yoo, H.-D.; Gerwick, W. H.; Kim, T.-S.; Nambu, M.; White, J. D. Tetrahedron Lett. 1995, 36, 1189-1192.
6. (f) Bicyclohumulenone: Matsuo, A.; Nozaki, H.; Nakayama, M.; Kushi, Y.; Hayaski, S. J. Chem. Soc., Chem. Commun. 1979, 174-175.
7. (g) Hybridalactone: Higgs, M. D.; Mulheirn, L. J. Tetrahedron 1981, 37, 4259-4262.
8. (h) Constanolactones A and B: Nagle, D. G.; Gerwick, W. H. Tetrahedron Lett. 1990, 31, 2995-2998.
9. (i) Halicholactone and neochalicholactone: Kigoshi, H.; Niwa, H.; Yamada, K.; Stout, T. J.; Clardy, J. Tetrahedron Lett. 1991, 32, 2427-2430.