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research article
Copper-Catalyzed Cyanoalkylative Aziridination of N-Sulfonyl Allylamines
May 26, 2020
Reaction of N-arylsulfonyl allylamines with alkyl nitriles in the presence of di-tert-butyl peroxide (DTBP) and a catalytic amount of copper salt afforded homologated aziridines in 43-86% yield. A sequence involving addition of the in situ generated cyanomethyl radical to the double bond followed by a copper-mediated intramolecular C-N bond formation accounted for the reaction outcome. 2,3-Disubstituted allylamines were converted to trisubstituted aziridines in a stereoselective manner. Starting from enantioenriched allylamines, chiral aziridines were obtained diastereoselectively.
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Type
research article
Web of Science ID
WOS:000535321000019
Authors
Publication date
2020-05-26
Publisher
Published in
Volume
362
Issue
11
Start page
2205
End page
2210
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
June 5, 2020