Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes

Aaron Roth; Scott E. Denmark

doi:10.1021/jacs.9b07019

Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes

Aaron Roth, Scott E. Denmark

Chemistry

Research output: Contribution to journal › Article

Abstract

A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.

Original language	English (US)
Pages (from-to)	13767-13771
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	141
Issue number	35
DOIs	https://doi.org/10.1021/jacs.9b07019
State	Published - Sep 4 2019

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.9b07019

Fingerprint Dive into the research topics of 'Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes'. Together they form a unique fingerprint.

Cite this

@article{12da9d06a8084eb0987a587b4de40aff,

title = "Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes",

abstract = "A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.",

author = "Aaron Roth and Denmark, {Scott E.}",

year = "2019",

month = sep,

day = "4",

doi = "10.1021/jacs.9b07019",

language = "English (US)",

volume = "141",

pages = "13767--13771",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "35",

}

TY - JOUR

T1 - Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes

AU - Roth, Aaron

AU - Denmark, Scott E.

PY - 2019/9/4

Y1 - 2019/9/4

N2 - A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.

AB - A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.

UR - http://www.scopus.com/inward/record.url?scp=85071788661&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85071788661&partnerID=8YFLogxK

U2 - 10.1021/jacs.9b07019

DO - 10.1021/jacs.9b07019

M3 - Article

C2 - 31433174

AN - SCOPUS:85071788661

VL - 141

SP - 13767

EP - 13771

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 35

ER -