Catalytic Asymmetric Acylation of Racemic Secondary Alcohols with Benzoyl Chloride in the Presence of a Chiral Diamine

• Tomohumi Sano

  Faculty of Science, Ibaraki University2-1-1 Bunkyo, Mito

• Keisuke Imai

  Faculty of Science, Ibaraki University2-1-1 Bunkyo, Mito

• Kousaburo Ohashi

  Faculty of Science, Ibaraki University2-1-1 Bunkyo, Mito

• Takeshi Oriyama

  Faculty of Science, Ibaraki University2-1-1 Bunkyo, Mito

Abstract

Nonenzymatic kinetic resolution of racemic secondary alcohols is an efficient synthetic method to obtain optically active compounds in organic chemistry. Catalytic asymmetric acylation of racemic secondary alcohols has been successfully performed with achiral benzoyl chloride in the presence of only 0.3 mol% of chiral diamine (3) derived from (S)-proline, combined with 0.5 equivalent of triethylamine. This asymmetric acylation of various racemic cyclic secondary alcohols, 5, 6, or 8 membered cycloalkanols (1a–1c), hydroxyesters (1d and 1e), and bromohydrins (1f and 1g) gave the corresponding optically active benzoates (84–97% ee) and unreacted alcohols (79–95% ee). Racemic acyclic secondary alcohols (1h–1j) were also acylated in moderate enantioselectivity.

Journal

• Chemistry Letters

  Chemistry Letters 28 (3), 265-266, 1999-03-01

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360846644039777664
• NII Article ID: 10004340442
• NII Book ID: AA00603318
• DOI: 10.1246/cl.1999.265
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/28/3/265/56075741/cl.1999.265.pdf
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  • CiNii Articles