145299-85-0Relevant academic research and scientific papers
Stereoconvergent negishi arylations of racemic secondary alkyl electrophiles: Differentiating between a CF3 and an alkyl group
Liang, Yufan,Fu, Gregory C.
supporting information, p. 9523 - 9526 (2015/08/18)
In this report, we establish that a readily available nickel/bis(oxazoline) catalyst accomplishes a wide array of enantioconvergent cross-couplings of arylzinc reagents with CF3-substituted racemic secondary alkyl halides, a process that necessitates that the chiral catalyst be able to effectively distinguish between a CF3 and an alkyl group in order to provide good ee. We further demonstrate that this method can be applied without modification to the catalytic asymmetric synthesis of other families of fluorinated organic compounds.
Trifluoromethyl ketones from enolizable carboxylic acids via enediolate trifluoroacetylation/decarboxylation
Reeves, Jonathan T.,Song, Jinhua J.,Tan, Zhulin,Lee, Heewon,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 9476 - 9478 (2009/04/06)
(Chemical Equation Presented) Primary and secondary (enolizable) carboxylic acids were converted in a single step to trifluoromethyl ketones. Treatment of the acid with 2.2 equiv of LDA generated an enediolate that was trifluoroacetylated with EtO2CCF3. Quenching the reaction mixture with aqueous HCl resulted in rapid decarboxylation and provided the trifluoromethyl ketone product in good yield. The process may be performed at -20°C with a slight reduction in yield. The reaction was extended to the preparation of pentafluoroethyl and chlorodifluoromethyl ketones.
Synthesis of lactones with a chlorodifluoromethyl group
Kimura, Mitsuo,Tominaga, Tsuneyoshi,Kitazume, Tomoya
, p. 135 - 139 (2007/10/03)
Synthetic routes to lactones with a chlorodifluoromethyl group via S N2′, oxidation and lactonization reactions, were described.
Lewis Acid Catalyzed Aldol-Type Reaction of 1,1-Difluorovinyl Methyl Ether Derivatives
Kodama, Yoshitoshi,Yamane, Hidefumi,Okumura, Masato,Shiro, Motoo,Taguchi, Takeo
, p. 12217 - 12228 (2007/10/02)
In the presence of Lewis acid, such as SbCl5, SbCl6*NAr3 or Cu(OTf)2, difluorovinyl methyl ether (1,1-difluoro-2-methoxy-1-alkene) 1 reacted with carbonyl compounds to give O-methylated aldol-type products 3 in good yields, while Lewis acid, such as TMSOT
A microbially-based approach for the synthesis of chiral secondary alcohols bearing the difluoromethyl or chlorodifluoromethyl group
Kitazume, Tomoya,Asai, Masatomo,Tsukamoto, Takashi,Yamazaki, Takashi
, p. 271 - 284 (2007/10/02)
A synthetic approach to both enantiomers of the secondary alcohols , involving the stereoselective hydrolysis of ester derivatives, is described.The absolute configurations of these difluoromethylated or chlorodifluoromethylated molecules were determined.
