From Tin to Lithium: Synthetic Applications and Dynamics of Chiral Organometallics

by Gawley, Robert E.

Carbanions in which the metal-bearing carbon are stereogenic are finding interesting and important applications in synthetic methodol., esp. asym. synthesis. Some of these have been achieved in our lab, and will be briefly summarized. The dynamics of chiral organolithiums are particularly interesting, in that they are amenable to dynamic resoln. However, identifying the conditions for achieving a dynamic resoln. are, for the most part, empirical. To lay the foundation for understanding the dynamics of these interesting species, we have undertaken a systematic investigation of the thermodn. parameters for carbanion inversion, and found some interesting trends, including a couple of surprises.