121892-75-9Relevant academic research and scientific papers
Copper-catalyzed asymmetric allylic alkylation of halocrotonates: Efficient synthesis of versatile chiral multifunctional building blocks
Den Hartog, Tim,Macia, Beatriz,Minnaard, Adriaan J.,Feringa, Ben L.
scheme or table, p. 999 - 1013 (2010/08/07)
The highly enantioselective synthesis of amethyl-substituted esters is reported in up to 90% yield and up to 99% ee using copper-TaniaPhos as chiral catalyst. The transformation proved scalable to at least 6.6 mmol (1.7 g scale). The products of this transformation have been further elaborated to multifunctional building blocks with a single (branched esters and acids) or multiple stereogenic centers (vicinal dimethyl esters, as well as, hydroxy- or iodosubstituted lactones).
Stereoseleetive synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes
Liu, Da-Neng,Tian, Shi-Kai
supporting information; experimental part, p. 4538 - 4542 (2009/12/25)
A study was conducted to demonstrate stereoselective synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes. Triphenylphosphine, α-halo carbonyl compounds, and methyl acrylate were added to a solution of aldehyde in chloroform or 1-propanol under nitrogen at room temperature. The resulting mixture was stirred at the specified temperature until transformation was completely observed by thin layer chromatography (TLC) analysis. The mixture was cooled to room temperature and purified by column chromatography on silica gel, eluting with petroleum ether/ethyl acetate. The study demonstrated that the first one-pot and three-component reaction of aldehydes, α-haloacetates, and terminal alkenes was developed in the presence of phenylphosphine to produce a wide range of trisubstituted alkenes with significant stereoselectivity.
Esterification of carboxylic acids catalyzed by in situ generated tetraalkylammonium fluorides
Ooi, Takashi,Sugimoto, Hayato,Doda, Kanae,Maruoka, Keiji
, p. 9245 - 9248 (2007/10/03)
Esterification of carboxylic acids with alkyl halides can be efficiently catalyzed by tetrabutylammonium fluoride (TBAF) generated in situ from tetrabutylammonium hydrogensulfate (TBAHSO4) and KF·2H2O in THF. The general applicability and the characteristic feature of this approach has been amply demonstrated.
