A cascade approach to cyclic aminonitrones: reaction discovery, mechanism, and scope.
Treatment of omega-epoxynitriles with hydroxylamine affords cyclic aminonitrones in a single step and with high stereoselectivity. The scope of this novel transformation was explored in a series of examples. The aminonitrone products were shown to be useful substrates for further selective elaboration.
Sharma
Rojita
R
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA.
Bulger
Paul G
PG
McNevin
Michael
M
Dormer
Peter G
PG
Ball
Richard G
RG
Streckfuss
Eric
E
Cuff
James F
JF
Yin
Jingjun
J
Chen
Cheng-yi
CY
D018360:Crystallography, X-Ray; D003500:Cyclization; D015195:Drug Design; D019428:HIV Integrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000737:chemistry*; D011760:Pyrrolidinones / Q000737:chemistry; D000068898:Raltegravir Potassium
D019428:HIV Integrase Inhibitors; D011744:Pyrimidinones; D011760:Pyrrolidinones; D000068898:Raltegravir Potassium