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Synlett 1994; 1994(1): 87-88
DOI: 10.1055/s-1994-22749
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Chelation Controlled Reactions between Hydroxy- and Alkoxy-ketones and Prop-2-enyltin Trihalides

David J. Hallett* , Eric J. Thomas
  • *The Department of Chemistry, The University of Manchester, Manchester, M13 9PL, U.K.
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Publication Date:
22 March 2002 (online)

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α-Hydroxy- and α-alkoxy-ketones react with prop-2-enyltin trihalides at -78 °C in dichloromethane to give 1,1-disubstituted but-3-enols; unsubstituted ketones don't react under these conditions. Chelation control was observed for chiral hydroxy- and alkoxy-ketones.

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