Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams.
The development of a versatile method for the preparation of five- to eight-membered hydroxy lactams that involves the iodine(III)-mediated oxamidation of unsaturated O-alkyl hydroxamates is described. This transformation, which is believed to proceed through the intermediacy of singlet nitrenium and bicyclic N-acyl-N-alkoxyaziridinium ions, is both stereospecific and highly regioselective in most of the 22 cases examined.
Wardrop
Duncan J
DJ
University of Illinois at Chicago, Department of Chemistry, 845 West Taylor Street, Room 4500, Chicago, Illinois 60607-7061, USA. wardropd@uic.edu
Bowen
Edward G
EG
Forslund
Raymond E
RE
Sussman
Adam D
AD
Weerasekera
Samanthi L
SL
D003500:Cyclization; D006877:Hydroxamic Acids / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure
D006877:Hydroxamic Acids; D007769:Lactams