CHIRAL, NONRACEMIC, 2-LITHIOPIPERIDINES AND 2-LITHIOPYRROLIDINES - REMARKABLY STABLE CARBANIONS WITH CONSIDERABLE SYNTHETIC POTENTIAL

Functionalized organolithiums are becoming more and more important as reagents in organic synthesis as methods for their preparation are exp anded, and as the number of stereoselective reactions in which they pa rticipate grows. In the alpha-aminoorganolithium field, the so-called ''unstabilized'' species - those that are not chelated and not stabili zed by re-sonance or a dipole-exhibit extraordinary configurational st ability and undergo efficient reactions with a wide variety of electro philes. They also undergo sigmatropic rearrangements if appropriately substituted. This chapter reviews the chemistry of these species.