Michael Addition of Amine Derivatives to Conjugate Phosphinyl and Phosphonyl Nitrosoalkenes. Preparation of alpha-Amino Phosphine Oxide and Phosphonate Derivatives

摘要

The synthesis of nitrosoalkenes derived from phosphine oxides and phosphonates generated through base mediated dehydrohalogenations of readily available alpha-halooximes is reported. These highly reactive intermediates act as Michael acceptors toward nucleophilic reagents such as ammonia, amines, and optically active amino esters, furnishing alpha-amino phosphine oxides and phosphonates in a highly regioselective fashion.