Asymmeric Formal [3+3]-Cycloaddition Reactions of Nitrones with Electrophilic Vinylcarbene Intermediates

被引：144

作者：

Wang, Xiaochen ^{[1
]}

Xu, Xinfang ^{[1
]}

Zavalij, Peter Y. ^{[1
]}

Doyle, Michael P. ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 41期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; DIELS-ALDER REACTION; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; AZOMETHINE IMINES; CYCLOPROPANATION; ENHANCEMENT; CATALYST; COMPLEX;

D O I：

10.1021/ja207664r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a beta-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones.

引用

页码：16402 / 16405

页数：4

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