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.
University of Illinois at Chicago, Department of Chemistry, 845 West Taylor Street, Room 4500, Chicago, Illinois 60607-7061, USA. wardropd@uic.edu
Duncan J
DJ
Wardrop
Edward G
EG
Bowen
Raymond E
RE
Forslund
Adam D
AD
Sussman
Samanthi L
SL
Weerasekera
D003500:Cyclization; D006877:Hydroxamic Acids / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure
D006877:Hydroxamic Acids; D007769:Lactams