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Catalytic asymmetric thiofunctionalization of unactivated alkenes.

ABSTRACT: Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles.

SUBMITTER: Denmark SE

PROVIDER: S-EPMC3187834 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Catalytic asymmetric thiofunctionalization of unactivated alkenes.

Denmark Scott E SE Kornfilt David J P DJ Vogler Thomas T

Journal of the American Chemical Society 20110914 39

Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles. ...[more]

PMID: 21859086

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