Favorskii rearrangement of a highly functionalized meso-dihaloketone |
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| Authors: | Paula M Tomlin David J Davies Martin D Smith |
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| Institution: | 1. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK;2. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK;3. GlaxoSmithKline, Ion Channel Group, Discovery Medicinal Chemistry, Gunnels Wood Road, Stevenage, Herts SG1 2NY, UK |
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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. |
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