Tetrahedron

Diastereofacial selectivity in the reaction of chiral N-trimethylsilyl imines with ester enolates: Preparation of trans-azetidin-2-ones in high stereocontrolled fashion.

G Cainelli, M Panunzio, E Bandini, G MartelIi, G Spunta

Index: Cainelli; Panunzio; Bandini; Martelli; Spunta Tetrahedron, 1996 , vol. 52, # 5 p. 1685 - 1698

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Citation Number: 39

Abstract

Highly efficient chiral ester enolate-imine condensation, giving 3, 4-disubstituted β-lactams with excellent trans-syn or trans-anti diastereoselectivity, is reported. The chiral information is included in the electrophilic partner of the condensation, nominally chiral α-, β-silyloxy-or alkoxy-N-trimethylsilyl-imines. The high diastereofacial selectivity is determined by the correct choice of the metal cations present in the reaction medium and the very nature of ...