Stereoselective conjugate addition of an α-sulfinyl carbanion to α,β-unsaturated esters: Asymmetric synthesis of cycloalkanecarboxylates

Article abstract of DOI:10.1055/s-1997-6144

The reaction of lithiated (R)-2-(trimethylsilyl)ethyl p-tolyl sulfoxide 1 with α,β-unsaturated esters gives 1,4-conjugate addition products as single stereoisomers, whereas the reaction of 1 with 4-, 6-, or 7-haloalkenoates affords cyclopropane-, cyclopen