Synlett 1995; 1995(4): 372-374
DOI: 10.1055/s-1995-4954
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.

Catalytic Enantioselective Protonation of Simple Enolate with Chiral Imide1

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

Publication History

Publication Date:
31 December 2000 (online)

The catalytic enantioselective protonation of simple enolate was achieved using chiral proton source, (S,S)-imide 1 which possesses an asymmetric 2-oxazoline ring, as a catalyst. Treatment of the lithium enolate 4 with (S,S)-imide 1 (0.1 equiv) followed by addition of bulky phenol derivative or β-diketone as achiral proton source (1 equiv) afforded (R)-2,2,6-trimethylcyclohexanone (5) with high enantioselectivity.