Hydride shift generated oxonium ions:: Evidence for mechanism and intramolecular trapping experiments to form trans THF derivatives

被引：25

作者：

Donohoe, Timothy J. ^{[1
]}

Williams, Oliver ^{[1
]}

Churchill, Gwydion H. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 15期

关键词：

hydride shift; oxonium ion; reduction; stereoselectivity; synthetic methods;

D O I：

10.1002/anie.200705340

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Switching sides: cis THF derivatives produced from the oxidative cyclization of dienes and diols can be transformed into the corresponding trans heterocycles through a 1,2-hydride shift and intramolecular trapping with a hydride nucleophile (see scheme). Moreover, organometallic compounds can be used to trap the oxonium ion generated in this way so that it is possible to introduce various groups at the C-2 position with control of stereochemistry. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2869 / 2871

页数：3

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