Download PDF
Synlett 1997; 1997(8): 956-958
DOI: 10.1055/s-1997-937
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Diastereoselective Protonation of Chiral Enolate with Chiral Imides

Akira Yanagisawa, Tsuyoshi Watanabe, Tetsuo Kikuchi, Takeshi Kuribayashi, Hisashi Yamamoto*
  • *Graduate School of Engineering, Nagoya University, CREST, Japan, Chikusa, Nagoya 464-01, Japan
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Described herein is a diastereoselective protonation of a chiral enolate with chiral imides. When the lithium enolate of (-)-menthone was protonated by (S,S)-imide 1 or (R)-imide 9, cis-ketone 7 was the major product formed (trans-product 6:cis-product 7 = 26:74 ~19:81). In contrast, a high trans-selectivity (6:7 = 93:7 ~ 97:3) was obtained for the reaction with (R,R)-imide 8 or (S)-imide 10. The catalytic process of this diastereoselective protonation has been realized using a catalytic amount of these chiral imides and stoichiometric amount of an achiral proton source.

diastereoselective protonation - chiral enolate - chiral imide - catalytic protonation - achiral proton source