Reactions with aziridines, 46. Ring opening of stilbene imines by thiophenolate

Abstract

Abstract Ring opening by thiophenolate of cis ‐ trans pairs of stilbene imines proceeds stereospecifically irrespective of the kind of mono activation by the phenylsulfonyl group ( 1 ), by the benzoyl group ( 2 ), or by protonation of the aziridine base ( 3 ). In accordance with complete Walden inversion, the sole product from the cis isomer is always a diastereomer of the sole product from the trans isomer. The diastereomers obtained from 3 are correlated with the respective diastereomers obtained from 2 .