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
收藏
页码：1101 / 1105
页数：5
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