ASYMMETRIC CONJUGATE ADDITION REACTION BY THE USE OF (S)-γ-TRITYLOXYMETHYL-γ-BUTYROLACTAM AS A CHIRAL AUXILIARY

Article abstract of DOI:10.1016/S0040-4039(00)84021-6

(S)-γ-Trityloxymethyl-γ-butyrolactam (2) serves as a chiral auxiliary in the conjugate addition reaction of the corresponding imide (3) of α,β-unsaturated carboxylic acids with Grignard reagents in the presence of CuBr-SMe2 in THF to give, after hydrolysis, the β,β-disubstituted carboxylic acids (5) with predictable absolute configuration and high enantiomeric excess.