Favorskii rearrangement of a highly functionalized meso-dihaloketone

  • Tomlin P
  • Davies D
  • Smith M
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Abstract

This paper describes studies on the feasibility of an asymmetric Favorskii rearrangement of a meso-dihaloketone substrate. In the racemic series, metal amide bases in the presence of amines give poor to reasonable yields of ring-contracted unsaturated cyclopentyl amides, whilst amines in aqueous solvent mixtures afford cyclopentyl amides in good to excellent yields. A range of chiral non-racemic amines are screened, a tiny diastereo-bias is observed and a tentative mechanistic rationale for the diastereoselective process is proposed. © 2009 Elsevier Ltd. All rights reserved.

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Authors

  • Paula M. Tomlin

  • David J. Davies

  • Martin D. Smith

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