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Synthesis 1992; 1992(9): 852-858
DOI: 10.1055/s-1992-26246
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2,2-Dimethyl-1,3-oxathiane 3,3-Dioxide: A γ-Hydroxypropyl Anion Equivalent

Kaoru Fuji* , Yoshihide Usami, Yoshimitsu Kiryu, Manabu Node
  • *Institute for Chemical Research, Kyoto University, Uji, Kyoto 611, Japan
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Publikationsdatum:
17. September 2002 (online)

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The reaction of 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide with various electrophiles is presented. Acylation of the anion provided labile 4-acyl-2, 2-dimethyl-1,3-oxathiane 3,3-dioxides which underwent desulfonation with silica gel to produce γ-hydroxy ketones with three carbon unit elongation. Thus, 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide was shown to be a useful synthetic equivalent of a γ-hydroxypropyl anion. Methyl esters proved to be the best acylating agents in this reaction. Synthetic utility of this carbon chain elongation was illustrated by the syntheses of dl-lanceol and dl-dihydrojasmone.