Remote stereocontrol by sulfinyl groups: asymmetric alkylation of chiral 2-p-tolylsulfinyl benzyl carbanions

Alkylation reactions of the benzyllithiums derived from enantiomerically pure 2-p-tolylsulfinyl alkylbenzenes have been carried out with excellent yields and high de. A lithiation-substitution sequence, stereochemically controlled by a remote sulfoxide, accounts for the experimental results.