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Synlett 1993; 1993(10): 728-730
DOI: 10.1055/s-1993-22586
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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
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Publication Date:
19 March 2002 (online)

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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.