A highly diastereoselective decarboxylative mannich reaction of ß-keto acids with optically active N-sulfinyl α-imino esters.

ABSTRACT

A range of protected γ-oxo-α-amino esters have been prepared in a highly regio- and stereoselective manner through the decarboxylative Mannich reaction of ß-keto acids with optically active N-tert-butanesulfinyl α-imino esters in the presence of 3 mol % La(OTf)(3) or 5 mol % Y(OTf)(3) at 20 °C. Preliminary mechanistic studies indicate that the reaction proceeds through imine addition followed by decarboxylation.