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Synlett 1991; 1991(11): 836-840
DOI: 10.1055/s-1991-20897
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Chiral Recognition Reactions of Homochiral Sulphinate Esters: A Study of the Reaction Between the Enolate, and the Anion of the Corresponding Dimethylhydrazone, Derived from 4-tert-Butylcyclohexanone and (1R,2S,5R)-(-)-Menthyl-(S)-p-Tolylsulphinate

Martin Wills* , Ian D. Linney, Christopher Lacy, Mary F. Mahon, Kieran C. Molloy
  • *School of Chemistry, University of Bath, Claverton Down, Bath, Avon, BA2 7AY, England
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Publication Date:
07 March 2002 (online)

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The reaction between (excess) racemic sodium enolate of 4-tert-butylcyclohexanone and an enantiomerically pure sulphinate ester has been studied. The major product [4-tert-butyl-2-(p-tolylsulfinyl)cyclohexanone] from this reaction has been isolated and its structure confirmed by an X-ray crystallographic study. The relative configurations in this product indicate that sulphinate ester of S configuration reacts preferentially with the enolate of S configuration. The reaction is accompanied by epimerisation of the sulphinate ester, resulting in the overall formation of a racemic product. However this problem can be overcome by the use of the anion derived from the corresponding dimethylhydrazone which furnishes, after hydrolysis, enantiomerically pure product of identical relative configuration.