Copper‐Catalyzed Cyanoalkylative Aziridination of N‐Sulfonyl Allylamines. Issue 11 (8th April 2020)

• Record Type: Journal Article
• Authors: Ha, Tu M.; Guo, Weisi; Wang, Qian; Zhu, Jieping
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 11(2020)
• Page Start: 2205
• Page End: 2210
• Publication Date: 2020-04-08
• Subjects: aziridine -- alkyl nitrile -- radical -- alkene -- homogeneous catalysis -- copper; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000276
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :