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 | |
| State | Published - Sep 4 2019 |
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ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes. / Roth, Aaron; Denmark, Scott E.
In: Journal of the American Chemical Society, Vol. 141, No. 35, 04.09.2019, p. 13767-13771.Research output: Contribution to journal › Article
}
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 -