Modified Preparation Method of Trifluoromethylated Propargylic Alcohols and Its Application to Chiral 2,6-Dideoxy-6,6,6-trifluorosugars

Article abstract of DOI:10.1021/jo00124a013

Convenient generation of 3,3,3-trifluoropropynyl anion was realized from 2-bromo-3,3,3-trifluoropropene, and the anion's reaction with various electrophiles proceeded in excellent isolated yields.One of the products, 1-(benzyloxy)-6,6,6-trifluoro-4-hexyn-3-ol (4b), was further employed for the diastereoselective construction of 2,6-dideoxy-6,6,6-trifluorosugars after enzymatic optical resolution and osmium dihydroxylation of the corresponding olefins.The strongly electron-withdrawing trifluoromethyl moiety, significantly affecting the nucleophilic nature of the neighbouring functionalities, allows to ready differentiation of hydroxy groups by routine chemical transfromation, which results in the shortening of the reaction sequence.