Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines

Scott E. Denmark, Hyung Min Chi

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)3826-3843
Number of pages18
JournalJournal of Organic Chemistry
Volume82
Issue number7
DOIs
StatePublished - Apr 7 2017

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Aniline Compounds
Nucleophiles
Enantioselectivity
Alkenes
Catalysts
Carrier concentration
Nitrogen
Chemical activation
Ions
Acids
Substrates

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines. / Denmark, Scott E.; Chi, Hyung Min.

In: Journal of Organic Chemistry, Vol. 82, No. 7, 07.04.2017, p. 3826-3843.

Research output: Contribution to journalArticle

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