Stereocontrolled fluorobenzylation of vinyl sulfones and α,β-unsaturated esters mediated by a remote sulfinyl group. Synthesis of functionalized enantiomerically pure benzylic fluorides.

A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with β-substituted vinyl sulfones and α,β-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure γ-fluorinated γ-phenylsulfones and γ-phenylesters bearing two chiral centers.