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Copper‐Catalyzed Cyanoalkylative Aziridination of N ‐Sulfonyl Allylamines
Author(s) -
Ha Tu M.,
Guo Weisi,
Wang Qian,
Zhu Jieping
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000276
Subject(s) - chemistry , intramolecular force , catalysis , stereoselectivity , medicinal chemistry , sulfonyl , yield (engineering) , copper , alkyl , peroxide , double bond , salt (chemistry) , polymer chemistry , organic chemistry , materials science , metallurgy
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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