Xingang Zhang, F. Qing, Y. Yu
Sep 20, 2000
Citations
0
Influential Citations
36
Citations
Journal
Journal of Organic Chemistry
Abstract
The treatment of α-bromo-α,β-unsaturated esters 2 with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-unsaturated esters 3. The trifluoromethylation of (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate (2e), which is derived from 1-(R)-glyceraldehyde acetonide, yields the key intermediate α-trifluoromethyl-α,β-unsaturated esters 3e. This is transformed into anomeric acetates 8a and 8b and is used for the synthesis of a number of 2‘,3‘-dideoxy-2‘-trifluoromethylnucleosides.