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

Org Lett

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

Published: August 2009

AI Article Synopsis

  • Treatment of omega-epoxynitriles with hydroxylamine leads to the formation of cyclic aminonitrones in a straightforward, highly selective manner.
  • The effectiveness and versatility of this reaction were tested through various examples.
  • The resulting aminonitrone products can be further modified, making them valuable for additional chemical applications.

Article 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.

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Source
http://dx.doi.org/10.1021/ol9010147DOI Listing

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