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Synlett 1991; 1991(2): 84-86
DOI: 10.1055/s-1991-20634
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Chelation-Mediated Facially Selective Cycloaddition Reactions of 2-Formyl-2-methyl-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:
07 March 2002 (online)

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2-Formyl-2-methyl-1,3-dithiane 1-oxides undergo very highly diastereoselective heterocycloaddition reactions with Danishefsky's diene (E-1-methoxy-3-trimethylsilyloxy-1,3-butadiene) mediated by magnesium bromide to give after mild acidic work-up 2-(3,4-dihydro-4-oxo-2H-pyran-2-yl)-2-methyl-1,3-dithiane 1-oxides.