Phosphinamide-Directed Stereoselective Benzylic Lithiation

Significance

Metalation of stabilized carbanions adjacent to nitrogen atoms can be efficiently used for the stereoselective synthesis of various important synthetic building blocks, such as protected amino acids or 1,2-amino alcohols. The authors demonstrated here the regioselective C_α-deprotonation of N-benzylphosphine amides for the preparation of various substituted benzylamines, which may serve as very interesting synthetic intermediates. When an α-phenylethylamine group is used as a chiral auxiliary, the reaction is highly diastereoselective and allows a simple enantioselective preparation of a variety of substituted benzylamines.