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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