Regiochemistry of nucleophilic opening of β-substituted styrene oxides with thiolate anions: model experiments in the synthesis of leukotriene analogues

Abstract

β-Substituted trans-styrene oxides are cleaved with thiolate anions highly regioselectively by attack at the α-carbon whereas the cis-isomers are cleaved by attack at the α- and β-carbons. Cysteine, in a suitably protected form, similarly cleaves β-substituted trans-styrene oxides, thus allowing the synthesis of a simple LTE model.