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Communication | Regular issue | Vol 27, No. 11, 1988, pp.2549-2556
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4709
Asymmetric Electrophilic α-Amidoalkylation 5: Improved Stereoselectivities through New Chiral Auxiliaries

Klaus Th. Wanner,* Annerose Kärtner, and Elmar Wadenstorfer

*Institut für Pharmazie und Lebensmittelchemie, Universität München, Sophienstraße 10, D-80333 München, Germany


Enamides of type 2 were employed in asymmetric α-amidoalkylation reactions with silyl enol ether 4 as nucleophile. Depending on the chiral auxiliary used, (R)-5/(S)-5 stereoselectivities up to 95/5 could be reached. Based on the obtained results a model for the transient acyliminium ion is proposed.