SEARCH FOR CONFIGURATIONALLY STABLE, ARACEMIC ALPHA-AMINO ORGANOLITHIUMS

The search for configurationally stable alpha-amino carbanions has led to an interesting observation of differing reactivity of diastereomer ic organolithiums and to the characterization of aracemic 2-lithio-N-m ethylpiperidine and 2-lithio-N-methylpyrrolidine as configurationally stable alpha-aminoorganolithiums. Details for the preparation of these and related alpha-lithioheterocycles, evaluation of their chemical an d configurational stability, and a preliminary evaluation of the stere oselectivity of their reactions with electrophiles is presented.