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

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• 作者：Andrew DeAngelis ; Michael T. Taylor ; Joseph M. Fox
• 刊名：Journal of the American Chemical Society
• 出版年：2009
• 出版时间：January 28, 2009
• 年：2009
• 卷：131
• 期：3
• 页码：1101-1105
• 全文大小：259K
• 年卷期：v.131,no.3(January 28, 2009)
• ISSN：1520-5126

文摘

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 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 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.