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Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines.

ABSTRACT: A method for the catalytic, enantioselective, intramolecular sulfenoamination of alkenes with aniline nucleophiles has been developed. The method employs a chiral, Lewis basic selenophosphoramide catalyst and a Brønsted acid co-catalyst to promote stereocontrolled C-N and C-S bond formation by activation of an achiral sulfenylating agent. Benzoannulated nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, and tetrahydrobenzazepines were prepared with high to excellent enantioselectivities. The impact of tether length and electron density of both the nucleophile and olefin on the reactivity, site selectivity, and enantioselectivity were investigated and interpreted in terms of substrate-dependent stereodetermining thiiranium ion formation or capture.

SUBMITTER: Denmark SE

PROVIDER: S-EPMC5388071 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines.

Denmark Scott E SE Chi Hyung Min HM

The Journal of organic chemistry 20170315 7

A method for the catalytic, enantioselective, intramolecular sulfenoamination of alkenes with aniline nucleophiles has been developed. The method employs a chiral, Lewis basic selenophosphoramide catalyst and a Brønsted acid co-catalyst to promote stereocontrolled C-N and C-S bond formation by activation of an achiral sulfenylating agent. Benzoannulated nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, and tetrahydrobenzazepines were prepared with high to excellent enanti ...[more]

PMID: 28294614

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