Tetrahedron Letters p. 1111 - 1114 (1988)
Update date:2022-09-26
Topics:
Funk, Raymond L.
Bolton, Gary L.
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 hydroboronation 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.
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