Tetrahedron letters

Synthesis of 4, 6-dialkyl-1, 3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti, anti-1, 2, 3-triols and syn-1, 3-diols

RL Funk, GL Bolton

Index: Funk, Raymond L.; Bolton, Gary L. Tetrahedron Letters, 1988 , vol. 29, # 10 p. 1111 - 1114

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Citation Number: 21

Abstract

Abstract The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide anti, anti-1, 2, 3-triols and syn, 1, 3-diols, respectively. This methodology has been exploited in the synthesis of (±)-endo-1, 3-dimethyl-2, 9-dioxabicyclo [3.3. 1] nonane.