Control of enantioselectivity through a hydrogen-bonded template in the vanadium(V)-catalyzed epoxidation of allylic alcohols by optically active hydroperoxides

被引：35

作者：

Adam, W

Beek, AK

Pichota, A

Saha-Möller, CR

Seebach, D

Vogl, N ^{[1
]}

Zhang, R

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[2] ETH Honggerberg, Organ Chem Lab, HCI, CH-8093 Zurich, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(03)00213-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The vanadiuin(V)-catalyzed asymmetric epoxidation of primary allylic alcohols by the optically active TADDOL-derived hydroperoxide as the asymmetric controller provides the corresponding (R)-epoxides in up to 72% ee. From this mechanistic study we conclude that this novel enantioselective oxygen transfer takes place via a hydrogen-bonded template, held together by the vanadium metal. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：1355 / 1361

页数：7

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