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The synthesis of chiral functionalised morpholine N-oxides using a tandem Cope elimination/reverse-Cope elimination protocol
Authors:Ian A O'Neil  Ed Cleator  Alan P Chorlton
Affiliation:a Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Crown Street, Liverpool L69 7ZD, UK
b Millennium Pharmaceuticals, 75, Sidney Street, Cambridge, MA, USA
Abstract:Hydroxylamine derivatives of (S)-prolinol have been generated using a Cope elimination. These undergo reverse-Cope elimination onto a pendant double bond to give morpholine N-oxides containing three contiguous chiral centres.
Keywords:Cope elimination   Reverse-Cope elimination   Amine oxides
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