Rh-Catalyzed Formation of Dioxolanes from -Alkyl Diazoesters: Diastereoselective Cycloadditions of Carbonyl Ylides with Selectivity

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• 作者：Andrew DeAngelis ; Patricia Panne ; Glenn P. A. Yap ; Joseph M. Fox
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：February 15, 2008
• 年：2008
• 卷：73
• 期：4
• 页码：1435 - 1439
• 全文大小：135K
• 年卷期：v.73,no.4(February 15, 2008)
• ISSN：1520-6904

文摘

Described here is a diastereoselective Rh-catalyzed method for the preparation of dioxolanes from -alkyl--diazoesters. This represents the first general method for generating carbonyl ylides from -diazoestersthat possess -hydrogens, as such diazo compounds typically give rise to alkenes via -hydride elimination.Subsequent cycloaddition with aromatic aldehydes gives tetrasubstituted dioxolanes with unusually highdiastereoselectivity. A model is set forth to explain the diastereoselectivity of the cycloaddition.