TY - JOUR
T1 - Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes
AU - Roth, Aaron
AU - Denmark, Scott E.
N1 - We are grateful to the National Institutes of Health (GM R35 127010) for generous financial support. We also thank the UIUC SCS support facilities (microanalysis, mass spectrometry, X-ray and NMR spectroscopy) for their assistance. A.R. acknowledges the NIH-NIGMS CBI Training Grant (T32-GM070421) as well as the NSF for a Graduate Fellowship (GRFP).
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.
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U2 - 10.1021/jacs.9b07019
DO - 10.1021/jacs.9b07019
M3 - Article
C2 - 31433174
AN - SCOPUS:85071788661
SN - 0002-7863
VL - 141
SP - 13767
EP - 13771
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 35
ER -