1,3-Polyol arrays via the stereoselective rearrangement of vinyl acetals |
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| Authors: | Yongda ZhangTomislav Rovis |
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| Affiliation: | Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA |
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| Abstract: | A series of 1,3-dioxanyl vinyl acetals were readily synthesized from the corresponding dioxanone by a reduction and in situ acylation followed by Petasis olefination. Treatment of these vinyl acetals with BF3·OEt2 results in an O to C rearrangement to form anti-3,5-dihydroxyketones while a mixture of Me3Al and BF3·OEt2 provides the corresponding syn relationship via a stereoretentive rearrangement. |
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| Keywords: | polyols Lewis acids diastereoselection |
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