Open AccessCatalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines
Author(s) -
Scott E. Denmark,
Hyung Min
Publication year - 2017
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.7b00391
Subject(s) - enantioselective synthesis , nucleophile , intramolecular force , chemistry , catalysis , olefin fiber , aniline , reactivity (psychology) , lewis acids and bases , selectivity , substrate (aquarium) , combinatorial chemistry , organic chemistry , medicinal chemistry , medicine , oceanography , alternative medicine , pathology , geology
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.