- A novel synthesis of fluorine-containing cyclopentenones via Pauson-Khand reaction
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Intermolecular Pauson-Khand reaction of fluoroalkylated alkynes with 2-norbornene or 2,5-norbornadiene at the reflux temperature of dichloroethane proceeded smoothly to give the corresponding cyclopentenone derivatives in high yields as a mixture of regio
- Konno, Tsutomu,Kida, Takumi,Tani, Akinori,Ishihara, Takashi
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p. 147 - 156
(2013/01/15)
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- Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes
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A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-cata
- Shimizu, Masaki,Higashi, Masahiro,Takeda, Youhei,Jiang, Guofang,Murai, Masahito,Hiyama, Tamejiro
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p. 1163 - 1165
(2008/03/13)
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- 2-Bromo-3,3,3-trifluoropropene: A facile trifluoromethylacetylene anion synthon
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The introduction of trifluoromethylacetylene units into organic compounds has been further studied and extended. The direct reaction of two equivalents of Lithium Diisopropylamide with 2-bromo-3,3,3-trifluoropropene gave lithium trifluoromethylacetylide, the anion of which was trapped in greater than 90% overall yield with a variety of electrophiles.
- Katritzky, Alan R.,Qi, Ming,Wells, Adam P.
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p. 145 - 147
(2007/10/03)
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- Modified Preparation Method of Trifluoromethylated Propargylic Alcohols and Its Application to Chiral 2,6-Dideoxy-6,6,6-trifluorosugars
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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.
- Yamazaki, Takashi,Mizutani, Kenji,Kitazume, Tomoya
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p. 6046 - 6056
(2007/10/03)
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- NEW FLUORIDE ION-CATALYZED REACTION OF F-ALKYLACETYLENES WITH SILYL ENOL ETHERS. AN EFFICIENT ROUTE TO F-ALKYL-SUBSTITUTED PROPAPGYLIC ALCOHOLS AND α-HYDROXY KETONES
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Treatment of F-alkylacetylenes, generated in situ from 1H-F-1-alkenephosphonates, with silyl enol ethers in the presence of a catalytic amount of tetrabutylammonium fluoride gives good yields of F-alkyl-substituted propargyl alcohols or 4-(1H-F-alkylidene)-1,3-dioxolane derivatives, the latter being converted to the corresponding α-hydroxy ketones.
- Ishihara, Takashi,Yamasaki, Yasuhiro,Ando, Teiichi
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