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Synlett 1997; 1997(3): 322-324
DOI: 10.1055/s-1997-768
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Chirality Transfer from Nitrogen to Carbon in the [2,3]-Meisenheimer Rearrangement

Jonathan E.H. Buston1 , Iain Coldham2 , Keith R. Mulholland3
  • 1Department of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, U.K.
  • 2Department of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, U.K., Fax 01392 263434; E-Mail I.Coldham@exeter.ac.uk
  • 3SmithKline Beecham Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, U.K.
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Publication History

Publication Date:
31 December 2000 (online)

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Oxidation of chiral, camphidin-based allylic tertiary amines gives rise to chiral tertiary amine-N-oxides, which undergo the [2,3]-Meisenheimer rearrangement with high levels of stereoselectivity. Reductive N,O-bond cleavage of the O-allyl-hydroxylamine gives access to the allylic alcohol unit.

Meisenheimer rearrangement - amine-N-oxide - allylic alcohol - camphidin auxiliary - chirality transfer