Protective group tuning in the stereoselective conversion of α-amino aldehydes into aminoalkyl epoxides

Abstract

Abstract Sulfonium and arsonium ylides of the type CH2=S(CH3)2 and CH2=As(Ph)3 react with doubly protected α-amino aldehydes 1 derived from amino acids to form aminoalkyl epoxides 3 / 4 , diastereofacial selectivity ranging between 86:14 and 95:5.