A cascade approach to cyclic aminonitrones: reaction discovery, mechanism, and scope

Rojita Sharma; Paul G Bulger; Michael McNevin; Peter G Dormer; Richard G Ball; Eric Streckfuss; James F Cuff; Jingjun Yin; Cheng-yi Chen

doi:10.1021/ol9010147

A cascade approach to cyclic aminonitrones: reaction discovery, mechanism, and scope

Org Lett. 2009 Aug 6;11(15):3194-7. doi: 10.1021/ol9010147.

Authors

Rojita Sharma¹, Paul G Bulger, Michael McNevin, Peter G Dormer, Richard G Ball, Eric Streckfuss, James F Cuff, Jingjun Yin, Cheng-yi Chen

Affiliation

¹ Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA.

PMID: 19572567
DOI: 10.1021/ol9010147

Abstract

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.

MeSH terms

Crystallography, X-Ray
Cyclization
Drug Design
HIV Integrase Inhibitors / chemical synthesis
HIV Integrase Inhibitors / chemistry*
Molecular Structure
Pyrimidinones / chemical synthesis
Pyrimidinones / chemistry*
Pyrrolidinones / chemistry
Raltegravir Potassium

Substances

HIV Integrase Inhibitors
Pyrimidinones
Pyrrolidinones
Raltegravir Potassium