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. 2003 Jul 10;5(14):2429-32.
doi: 10.1021/ol0346180.

Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans

Conor St J Barry  1 , Stuart R Crosby, John R Harding, Rachael A Hughes, Clare D King, Gregory D Parker, Christine L Willis
Affiliations

Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans

Conor St J Barry et al. Org Lett. .

Abstract

[reaction: see text] Reaction of homoallylic alcohols with aldehydes in the presence of TFA gives, after hydrolysis of the ester, 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans with the creation of three new stereocenters in a single-pot process. By varying the aldehyde component, a variety of functionalized side chains are installed at C-2. The utility of this approach is extended to the enantioselective synthesis of tetrahydropyrans with >99% ee.

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