Diastereoselective Synthesis of the Leu-Pro Type Phosphinyl Dipeptide Isostere

A diastereoselective synthesis of the Leu-Pro type phosphinyl dipeptide isostere in its protected form was achieved from stereodefined alpha-amino-H-phosphinate. The methodology involved a cross-coupling reaction with alkenyl triflate and subsequent diastereoselective hydrogenation of the alkene moiety, which capitalized on the phosphorus chirality.