Catalytic asymmetric acylation of racemic secondary alcohols with benzoyl chloride in the presence of a chiral diamine

被引：85

作者：

Sano, T ^{[1
]}

Imai, K ^{[1
]}

Ohashi, K ^{[1
]}

Oriyama, T ^{[1
]}

机构：

[1] Ibaraki Univ, Fac Sci, Mito, Ibaraki 3108512, Japan

来源：

CHEMISTRY LETTERS | 1999年 / 03期

关键词：

D O I：

10.1246/cl.1999.265

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 (la-lc), hydroxyesters (Id and le), and bromohydrins (If and Ig) 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.

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页码：265 / 266

页数：2

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