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(R)-4-phenyloxazolidin-2-thione: an efficient chiral auxiliary for [4+2] cycloaddition of 1-aminodiene and activated phosphonodienophiles |
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| Authors: | Jean-Christophe Monbaliu Daniel Peeters |
| Institution: | a Unité de Chimie organique et médicinale, Département de Chimie, Université catholique de Louvain, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium b Unité de Chimie structurale et des mécanismes réactionnels, Département de Chimie, Université catholique de Louvain, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium |
| Abstract: | 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. |
| Keywords: | Diels-Alder cycloaddition Aminodiene Stereoselective synthesis Microwave-assisted synthesis |
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