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Synlett 1990; 1990(8): 460-462
DOI: 10.1055/s-1990-21126
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Highly Diastereoselective Reduction of Ketones in 2-Acyl-2-alkyl-1,3-dithiane 1-Oxides

Philip C. Bulman Page* , Jeremy C. Prodger
  • *Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, England
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Publication Date:
08 March 2002 (online)

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2-Acyl-2-alkyl-1,3-dithiane 1-oxides undergo diastereoselective reduction upon treatment with diisobutylaluminium hydride to give the corresponding secondary alcohols. The sense of diastereoselectivity is commonly reversed by the presence of zinc chloride during the action of the reducing agent. In many cases diastereoselectivity is sufficiently high that the minor isomer could not be detected by 400 MHz 1H NMR spectroscopy.