Unusually Reactive and Selective Carbonyl Ylides for Three-Component Cycloaddition Reactions

被引：83

作者：

DeAngelis, Andrew ^{[1
]}

Taylor, Michael T. ^{[1
]}

Fox, Joseph M. ^{[1
]}

机构：

[1] Univ Delaware, Brown Labs, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 03期

关键词：

1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTIONS; AZOMETHINE YLIDES; ALPHA-DIAZOESTERS; ALDEHYDES; CYCLIZATION; DIOXOLANES; DICARBOMETHOXYCARBENE; CARBENOIDS;

D O I：

10.1021/ja807184r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Conditions are described for the Rh-catalyzed formation of highly functionalized dihydro- and tetrahydrofuran products via three-component reactions of alclehydes, alpha-alkyl-alpha-diazoesters, and dipolarophiles. The alkyl-substituted carbonyl ylides that are generated in this fashion are highly reactive in cycloaddition reactions and display a scope of reactivity that is much broader than the three-component reactions of carbonyl ylides derived from ethyl diazoacetate or alpha-aryl-alpha-diazoesters. The reactions of alkyl-substituted carbonyl ylides proceed with high regioselectivity and diastereoselectivity that are rationalized in terms of an asynchronous, endo-selective transition state.

引用

页码：1101 / 1105

页数：5

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