Chiral Selenide-Catalyzed, Highly Regio- and Enantioselective Intermolecular Thioarylation of Alkenes with Phenols

Enantioselective
electrophilic three-component thioarylation of
alkenes by chiral selenide catalysis with free phenols as arylating
sources is disclosed. A variety of chiral phenols were achieved in
high regio-, enantio-, and diastereoselectivities. Mechanistic studies
revealed that this transformation went through carbon nucleophilic
attack to give the products rather than the process of intramolecular
rearrangement of phenolic ether intermediates. The application of
this organocatalytic method in the alkylation of methoxy-substituted
benzenes elucidated its generality.