Asymmetric Michael addition of glycine imines via quaternary ammonium ion catalysis

The asymmetric Michael addition of glycine imine esters to simple α,β-unsaturated ketones via PTC is investigated. It is found that by employing 1 mol % of a chiral quaternary ammonium salt, derived from α-methylnaphthylamine in conjunction with Cs2CO3, high enantioselectivities can be obtained in conjugate additions involving simple alkylvinylketones.