Complementary Reactions of Allylic
Carbamates Using Palladium(II): Formation of Oxazolidinones
or Allylic Amides from a Common Precursor

Steven D. R. Christie; Adam D. Warrington; Christopher J. Lunniss

doi:10.1055/s-0028-1083282

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Synthesis 2009(1): 148-154
DOI: 10.1055/s-0028-1083282

PAPER

Complementary Reactions of Allylic Carbamates Using Palladium(II): Formation of Oxazolidinones or Allylic Amides from a Common Precursor

Steven D. R. Christie*^a, Adam D. Warrington^a, Christopher J. Lunniss^b
^a Departmentt of Chemistry, Loughborough University, Loughborough, LE11 3RF, UK
Fax: +44(1509)223925; e-Mail: s.d.christie@lboro.ac.uk;
^b GlaxoSmithKline, Gunnels Wood Road, Stevenage, SG1 2NY, UK

Further Information

Publication History

Received 24 October 2008
Publication Date:
12 December 2008 (online)

Abstract
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Abstract

The use of palladium to effect two different reactions on a common starting material is presented. With a copper oxidant, an aminohalogenation is achieved to produce oxazolidinones. When the copper is absent, a [3,3]-sigmatropic rearrangement takes place to produce allylic amides.

Key words

palladium - rearrangement - halogenation - amines - amides

References

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