Synthesis of unfunctionalized carbonated fragments containing two vicinal chiral centers: Stereocontrolled benzylation of vinylsulfones mediated by a remote sulfinyl group

摘要

One-pot benzylation of (E)-vinylsulfones with optically pure 2-p-tolylsulfinylbenzyl carbanions and desulfinylation with tBuLi, followed by desulfonylation of the resulting 1-sulfonylpropanes, provided acyclic hydrocarbons containing two connected chiral centers in very smooth conditions and almost complete control of the stereoselectivity (see scheme).