A dynamic kinetic esolution of allyl alcohols by the combined use of lipases and [VO(OSiPh3)3]

被引：112

作者：

Akai, S

Tanimoto, K

Kanao, Y

Egi, M

Yanamoto, T

Kita, Y

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

[2] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 16期

关键词：

allyl alcohols; asymmetric synthesis; dynamic kinetic resolution; lipases; vanadium;

D O I：

10.1002/anie.200503765

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Mix and match: A new type of dynamic kinetic resolution of racemic allyl alcohols uses a combination of lipases and [VO(OSiPh3)3] (1). The 1,3-transposition of allyl alcohols catalyzed by 1 gave thermodynamic mixtures of two regioisomers, which underwent highly enantio-and chemoselective esterification with lipases. Optically enriched allyl acetates were isolated in high yields. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2592 / 2595

页数：4

共 48 条

[1] Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition:: a concise asymmetric total synthesis of (-)-rosmarinecine [J].