Chiral Organometallic Reagents, VII. On the Configurational Stability of α-Methylbenzyllithium

α-Methylbenzyllithium (6) should possess either central or planar chirality. The rate of enantiomerization of 6 at — 78°C was found to be faster than its addition to the amide 7, the ketone 8, or to the aldehyde 10, according to a test based on kinetic resolution. The benzyllithium compound 6 thus behaves in THF essentially as a prochiral entity.