title: Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans.
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.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Conor St J
authors.initials: CS
authors.lastname: Barry
authors.forename: Stuart R
authors.initials: SR
authors.lastname: Crosby
authors.forename: John R
authors.initials: JR
authors.lastname: Harding
authors.forename: Rachael A
authors.initials: RA
authors.lastname: Hughes
authors.forename: Clare D
authors.initials: CD
authors.lastname: King
authors.forename: Gregory D
authors.initials: GD
authors.lastname: Parker
authors.forename: Christine L
authors.initials: CL
authors.lastname: Willis