N-heterocyclic carbene catalyzed C-C bond cleavage in redox esterifications of chiral formylcyclopropanes

被引：170

作者：

Sohn, Stephanie S. ^{[1
]}

Bode, Jeffrey W. ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 36期

关键词：

esterifications; N-heterocyclic carbenes; organocatalysis; ring-opening; synthetic methods;

D O I：

10.1002/anie.200601919

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A clean break: An N-heterocyclic carbene catalyzes the ring-opening of chiral non-racemic formylcyclopropanes, with simultaneous oxidation of the aldehyde function and without the need for stoichiometric reagents. The activated carboxylate intermediate is trapped by a variety of nucleophiles, thus leading to chiral esters, thioesters, or carboxylic acids (see scheme; DBU = 1,8-diazabicyclo-[5.4.0]undec-7-ene, EWG = electron-withdrawing group, Nu = nucleophile.) © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6021 / 6024

页数：4

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