Reactions of phenyldimethylsilyllithium with β-N,N-dimethylaminoenones

Abstract

Phenyldimethylsilyllithium reacts with the β-N,N-dimethylaminoenones 1 and 7, with the enal 5, and with ethyl β-N,N-dimethylaminoacrylate 9 to give the corresponding α,β-unsaturated carbonyl compounds with a β-phenyldimethylsilyl group, but in the last case only when the reaction mixture is given a mysteriously brief treatment with methyl iodide before workup.