Applications of the Baylis–Hillman reaction 2: a simple stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes

Abstract

Reaction of Grignard reagents with methyl 3-acetoxy-2-methylenealkanoates produces (2E)-2-substituted alk-2-enoates, whereas a similar reaction with 3-acetoxy-2-methylenealkanenitriles provides (2Z)-2-substituted alk-2-enenitriles in high (Z)-stereoselectivity.