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

Miyako Ogata; Tsuyoshi Yoshimura; Hiroyuki Fujii; Yoshio Ito; Tsutomu Katsuki

doi:10.1055/s-1993-22586

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

Miyako Ogata, Tsuyoshi Yoshimura, Hiroyuki Fujii, Yoshio Ito, Tsutomu Katsuki

Organic and Biological Chemistry

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13 Citations (Scopus)

Abstract

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 β-oxo amide (up to 65% ee) and the released 1 was recovered intact for reuse.

Original language	English
Pages (from-to)	728-730
Number of pages	3
Journal	Synlett
Volume	1993
Issue number	10
DOIs	https://doi.org/10.1055/s-1993-22586
Publication status	Published - Oct 1993

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Chiral Leaving Group: Synthesis of Optically Active Benzimidazole and its Application to Asymmetric Acylation",

abstract = "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 β-oxo amide (up to 65% ee) and the released 1 was recovered intact for reuse.",

author = "Miyako Ogata and Tsuyoshi Yoshimura and Hiroyuki Fujii and Yoshio Ito and Tsutomu Katsuki",

year = "1993",

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doi = "10.1055/s-1993-22586",

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T2 - Synthesis of Optically Active Benzimidazole and its Application to Asymmetric Acylation

AU - Ogata, Miyako

AU - Yoshimura, Tsuyoshi

AU - Fujii, Hiroyuki

AU - Ito, Yoshio

AU - Katsuki, Tsutomu

PY - 1993/10

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N2 - 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 β-oxo amide (up to 65% ee) and the released 1 was recovered intact for reuse.

AB - 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 β-oxo amide (up to 65% ee) and the released 1 was recovered intact for reuse.

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

Abstract

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