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• 作者：Jean-Christophe Monbaliu ; Raphaë ; l Robiette ; Daniel Peeters ; Jacqueline March ; -Brynaert
• 关键词：Diels– ; Alder cycloaddition ; Aminodiene ; Stereoselective synthesis ; Microwave-assisted synthesis
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：25 March 2009
• 年：2009
• 卷：50
• 期：12
• 页码：1314-1317
• 全文大小：546 K

文摘

A theoretical model for the facial selectivity of N-dienyl oxazolidin-2-(thi)one and thiazolidin-2-thione 2a–c is presented. Our analysis provides a clear understanding of factors controlling stereoselectivity in reaction of these dienes, and allows predictions of high diastereoselectivity in the case of oxazolidin-2-thionyl diene (2b). The application of this diene to the synthesis of β- and γ-aminophosphonic derivatives is then investigated. Under classical conditions or under microwave activation, the D–A reaction of diene 2b leads to aminophosphonic chirons with high regio- and stereoselectivities.