Unexpected reversal of stereochemistry observed in the addition of methallyltrimethylsilane to a chiral α-keto imide

Abstract

ABSTRACT A Lewis acid–promoted nucleophilic addition of methallyltrimethylsilane to a chiral α-keto imide proceeded with stereoselectivity opposite to that predicted from Soai's report. The difference in the structure of α-keto imides between Soai's and our cases might have affected the diastereofacial selectivity.