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

Abstract

Highly stereoselective conjugate addition of an enantio-pure metalated β-amino substituted amino nitrile to α,β-unsaturated esters, with subsequent silver nitrate induced hydrolysis of the amino nitrile adducts affords 3-substituted 5-amino-4-oxo-esters with high enantiomeric purity, thus achieving the overall asymmetric Michael addition of an α-amino-acyl carbanion.