Enantioselective synthesis of cyclic ethers through a vanadium-catalyzed resolution/oxidative cyclization

被引：67

作者：

Blanc, A ^{[1
]}

Toste, FD ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 13期

关键词：

kinetic resolution; natural products; oxidation; tetrahydrofurans; tetrahydropyrans;

D O I：

10.1002/anie.200503852

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Two steps, one catalyst: A vanadium(v)-oxo complex with a tridentate Schiff base as an additional ligand catalyzes the title reaction which transforms racemic bishomoallylic α-hydroxyesters into trans-tetrahydropyrans (THPs) and cis-tetrahydrofurans (THFs). This synthetic method provides an efficient asymmetric synthesis of cyclic ethers as demonstrated by the first enantioselective synthesis of (-)-pantofuranoid E. TBHP = tert-butylhydroperoxide. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：2096 / 2099

页数：4

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