Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Stereocontrolled Preparation of 2,6-Disubstituted 4-Methylenetetrahydropyrans by Lewis Acid Promoted Allylsilane-Acetal Cyclization

  • Published : 1998.08.20
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Abstract

The Lewis acid mediated intramolecular additions of allylsilanes to acetal substrates are described. Excellent regio- and diastereoselectivity are achieved by boron trifluoride promoted cyclization of allysilane-acetals 5 and 8 derived from hydroxy allysilances 3. Cyclizations occur in moderate to high yields, providing directr routes to cis-2, 6-disubstituted 4-methylenetetrahydropyrans 6 and 9.

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References

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