A remarkable stereocontrol during cobalt(II) chloride catalysed opening of cinnamoyl epoxides with N-substituted anilines

Abstract

The stereochemistry of the cobalt(II) chloride catalysed opening of cinnamoyl epoxides with N-substituted anilines is controlled by the para substituent of the aromatic ring attached to nitrogen atom. Thus the secondary amine having a para methoxy group cleaves the epoxide to afford the corresponding anti amino alcohol as the major product whereas amines containing para chloro, bromo, methyl or hydrogen substituents afford the syn amino alcohols as the major diastereomer.