Download PDF
Synlett 1993; 1993(10): 728-730
DOI: 10.1055/s-1993-22586
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.

Chiral Leaving Group: Synthesis of Optically Active Benzimidazole and its Application to Asymmetric Acylation

Miyako Ogata* , Tsuyoshi Yoshimura, Hiroyuki Fujii, Yoshio Ito, Tsutomu Katsuki
  • *Department of Chemistry, Faculty of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812, Japan
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Optically active benzimidazole (1) prepared from (R)-(-)-mandelic acid was found to serve as an effective chiral leaving group. For example, N-propionyl derivative of 1 reacted with amide-enolate to give optically active ß-oxo amide (up to 65% ee) and the released 1 was recovered intact for reuse.