Samarium Iodobinaphtholate: An Efficient Catalyst for Enantioselective Aza??Michael Additions of O??Benzylhydroxylamine to N??Alkenoyloxazolidinones

D Didier, A Meddour…

Index: Didier, Dorian; Meddour, Abdelkrim; Bezzenine-Lafollee, Sophie; Collin, Jacqueline European Journal of Organic Chemistry, 2011 , # 14 p. 2678 - 2684

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Citation Number: 9

Abstract

Abstract Samarium diiodide is an efficient catalyst for the aza-Michael addition of O- benzylhydroxylamine to α, β-unsaturated N-acyloxazolidinones leading to mixtures of the Michael adduct and the product resulting from its amidation. Samarium iodobinaphtholate catalyzed reactions selectively afford the Michael adducts with enantiomeric excesses up to 88%. An isoinversion effect with temperature is observed with the highest enantiomeric ...