Intramolecular PhI=O mediated copper-catalyzed aziridination of unsaturated sulfamates: a new direct access to polysubstituted amines from simple homoallylic alcohols.
[reaction: see text] Olefinic sulfamates derived from primary and secondary alcohols undergo intramolecular copper-catalyzed aziridination in the presence of iodosylbenzene to afford novel bicyclic fused aziridines. The latter were opened by various nucleophiles to give the corresponding substituted cyclic sulfamates, which in turn reacted, after nitrogen activation, with a second nucleophile at the carbon atom bearing the oxygen atom. Concomitant removal of the sulfonyloxy moiety thus gave access to polysubstituted amines.
Duran
Fernando
F
Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Leman
Loïc
L
Ghini
Alberto
A
Burton
Gerardo
G
Dauban
Philippe
P
Dodd
Robert H
RH
D000438:Alcohols / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D013451:Sulfonic Acids / Q000737:chemistry*
D000438:Alcohols; D000588:Amines; D001388:Aziridines; D001685:Biological Factors; D013451:Sulfonic Acids; D003300:Copper; C005741:sulfamic acid