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