Generation of a Configurationally Stable Chiral Benzyllithium Derivative, and the Capricious Stereochemistry of Its Electrophilic Substitution

Abstract

Depending on the electrophile, substitution of the chiral benzyllithium compound 2, which is configurationally stable in solution, takes place with retention or inversion of configuration. 2 was generated by deprotonation of the Corresponding optically active benzyl carbamate 1. The products 3 are of interest as synthetic building blocks. Cb  C(O)NiPr2.