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Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans
Conor St J Barry1, Stuart R Crosby, John R Harding
1School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Organic Letters
|July 5, 2003
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.