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Paper | Special issue | Vol 47, No. 2, 1998, pp.725-746
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)47
Enantioselective Access to Five- and Six-membered Nitrogen-containing Heterocycles, Based on the Asymmetric Michael Addition of Chiral Imines and Chiral Enamino Esters

Jean d'Angelo,* Christian Cavé, Didier Desmaële, Abdoulaye Gassama, Cyrille Thominiaux, and Claude Riche

*Unité de Chimie Organique Associé au CNRS, Centre d'Etudes Pharmaceutiques, Université de Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Chatenay-Malabry Cedex, France

Abstract

The addition reaction of chiral imines, (ent-10,48,70) and chiral enamino esters (52, 55, 73) with maleic anhydride (32), citraconic anhydride (57), α-chloroacrylonitrile (29), and nitroethylene (74), has been investigated. These condensations proved to be in general highly regio-, diastereo-, and enantioselective. In most cases the primary adducts underwent an in situ N-heterocyclization, allowing the enantioselective access to nitrogen-containing, five- and six-membered heterocycles.