The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/Aza Bicyclic Alkenes

被引：58

作者：

Zhang, Lei ^{[1
]}

Le, Christine M. ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 23期

基金：

加拿大自然科学与工程研究理事会;

关键词：

asymmetric catalysis; rhodium; silyl ketene acetals; strained molecules; OXABICYCLIC ALKENES; ESTERS; PODOPHYLLOTOXINS; NAPHTHOQUINONE; DERIVATIVES; ARYLATION;

D O I：

10.1002/anie.201400218

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium-catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene natural products.

引用

页码：5951 / 5954

页数：4

共 9 条

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[8] A comprehensive study of [2+2] cycloadditions and ene reactions of alkynyl chromium and tungsten carbene complexes with enol ethers and ketene acetals and of the stereochemistry of the electrocyclic ring opening of cyclobutenyl carbene complexes
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