94792-96-8Relevant academic research and scientific papers
Facile one-pot preparation of allylic alcohols with a fluorine-containing alkyl group at the γ-position
Yamazaki, Takashi,Ichikawa, Masashi,Kawasaki-Takasuka, Tomoko,Yamada, Shigeyuki
, p. 151 - 154 (2013/10/01)
A useful one-pot preparation method of allylic alcohols with fluorinated alkyl groups at the γ position was developed from the corresponding enoates by way of the DIBAL-mediated half reduction, followed by nucleophilic attack of Grignard reagents to aldehydes equilibrating with aluminium acetals.
Electronically promoted Payne rearrangement of 3-CF3-2,3- epoxyalcohols
Yamazaki, Takashi,Ichige, Tatsuro,Kitazume, Tomoya
, p. 4073 - 4076 (2007/10/03)
(Chemical Equation Presented) Smooth and selective Payne rearrangement was achieved for the above types of epoxyalcohols with a CF3 group so as to form thermodynamically more stable alkoxides, where the strongly electron-withdrawing nature of this moiety played a significantly important role and was proved to overcome increased steric instability of epoxides from syn-E to anti-Z isomers.
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.
