Unusually reactive and selective carbonyl ylides for three-component cycloaddition reactions

被引：0
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作者：
Deangelis, Andrew [1 ]
Taylor, Michael T. [1 ]
Fox, Joseph M. [1 ]
机构：
[1] Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, United States
来源：
Journal of the American Chemical Society | 2009年 / 131卷 / 03期
关键词：
Conditions are described for the Rh-catalyzed formation of highly functionalized dihydro- and tetrahydrofuran products via three-component reactions of aldehydes; α-alkyl-α-diazoesters; and dipolaro- philes. 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 α-aryl-α-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. © 2009 American Chemical Society;
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页码：1101 / 1105
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