94792-95-7Relevant academic research and scientific papers
Modified Preparation Method of Trifluoromethylated Propargylic Alcohols and Its Application to Chiral 2,6-Dideoxy-6,6,6-trifluorosugars
Yamazaki, Takashi,Mizutani, Kenji,Kitazume, Tomoya
, p. 6046 - 6056 (2007/10/03)
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.
HYDROMETALLATION OF 1-ALKYL-3-TRIFLUOROMETHYL PROPARGYL ALCOHOLS
Hanzawa, Yuji,Kawagoe, Kei-ichi,Tanahasi, Naomi,Kobayashi, Yoshiro
, p. 4749 - 4752 (2007/10/02)
The hydrometallation of trifluormethylated propargyl alcohol derivatives with metal hydride reagents proceeds smoothly to give cis-and trans-olefins on H2O quenching.The halodemetallation of intermediate formed in the reaction process was also examined.
