Asymmetric nucleophilic alpha-amino-acylation with metalated chiral amino nitriles: enantioselective synthesis of 3-substituted 5-amino-4-oxo-esters via asymmetric Michael addition

Highly stereoselective conjugate addition of an enantiopure metalated beta- amino substituted amino nitrile to alpha,beta-unsaturated esters, with subs equent silver nitrate induced hydrolysis of the amino nitrile adducts affor ds 3-substituted 5-amino-4-oxo-esters with high enantiomeric purity, thus a chieving the overall asymmetric Michael addition of an alpha-amino-acyl car banion.