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.
Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Fernando
F
Duran
Loïc
L
Leman
Alberto
A
Ghini
Gerardo
G
Burton
Philippe
P
Dauban
Robert H
RH
Dodd
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