Diastereo- and enantioselective allylic S(N') substitution by phenylacetic esters enolates

Article abstract of DOI:10.1016/S0957-4166(00)82008-X

The Anti-Michael S(N') substitution of γ-bromo-α,β-unsaturated esters 1a-c by Li t.butyl phenylacetater enolate is highly diastereoselective. Asymmetric synthesis can be performed (ee ≥ 95%) using the enantiomerically pure (1'R,2'S) 2-phenyl cyclohexyl ester 1c.