✍ Scribed by Jean-Christophe Monbaliu; Raphaël Robiette; Daniel Peeters; Jacqueline Marchand-Brynaert
No coin nor oath required. For personal study only.
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 b-and c-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.
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## Abstract An efficient enantioselective synthesis of 3‐acetoxy __trans__‐__β__‐lactams **7a** and **7b** __via__ [2+2] cycloaddition reactions of imines **4a** and **4b**, derived from a polycyclic aromatic amine and bicyclic chiral acid obtained from (+)‐car‐3‐ene, is described. The cycloadditio