Tert-butylsulfonamide. A new nitrogen source for catalytic aminohydroxylation and aziridination of olefins.
[reaction: see text] The N-chloramine salt of tert-butylsulfonamide has been shown to be an efficient nitrogen source and the terminal oxidant for catalytic aminohydroxylation and aziridination of olefins, resembling closely Chloramine-T by its behavior in these catalytic reactions. The sulfonyl-nitrogen bond in the product or its derivatives is easily cleaved under mild acidic conditions, allowing for facile liberation of the amino group.
Gontcharov
A V
AV
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Liu
H
H
Sharpless
K B
KB
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis; D002384:Catalysis; D002700:Chloramines / Q000737:chemistry; D006900:Hydroxylation; D009584:Nitrogen / Q000737:chemistry*; D016877:Oxidants; D013449:Sulfonamides / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry
D000475:Alkenes; D000588:Amines; D001388:Aziridines; D002700:Chloramines; D016877:Oxidants; D013449:Sulfonamides; D014105:Tosyl Compounds; C016300:chloramine-T; C408993:tert-butylsulfonamide; D009584:Nitrogen