1.
Org Lett
; 6(23): 4269-72, 2004 Nov 11.
Artículo
en Inglés
| MEDLINE
| ID: mdl-15524460
RESUMEN
Direct precursors to analogues of pentopyranoses, 6-deoxyhexoses, and hexoses, in which a CF(2) center replaces the pyranose oxygen, have been synthesized rapidly from trifluoroethanol. A simple scaleable allylation reaction delivers ethers which undergo dehydrofluorination/metalation, followed by addition to either acrolein or cinnamaldehyde, to afford allylic alcohols. Fluorine-assisted [3,3]-rearrangement followed by reduction with sodium borohydride delivers diols, which undergo RCM smoothly to afford cyclohexene diols.