140630-67-7Relevant academic research and scientific papers
Titanocene-promoted intermolecular couplings of epoxides with nitriles. An easy access to β-hydroxyketones
Fernandez-Mateos,Encinas Madrazo,Herrero Teijon,Rubio Gonzalez
experimental part, p. 3913 - 3918 (2009/10/20)
(Chemical Equation Presented) Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of β-hydroxyketones. The conditions of this "aldol- like" reaction are mild enough to avoid the dehydration of the β-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.
TBD-catalyzed direct 5- and 6-enolexo aldolization of ketoaldehydes
Ghobril, Cynthia,Sabot, Cyrille,Mioskowski, Charles,Baati, Rachid
supporting information; experimental part, p. 4104 - 4108 (2009/05/27)
Treatment of unfunctionalized acyclic ketoaldehydes with a catalytic amount of 1,5,7-triazabicyclo[4.4.0]dec-5-ene induces a direct intramolecular 5- and 6-enolexo aldolization, furnishing 2-ketocyclopentanols and 2-ketocyclohexanols in good-to-excellent yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Palladium-catalyzed asymmetric silaborative C-C cleavage of meso-methylenecyclopropanes
Ohmura, Toshimichi,Taniguchi, Hiroki,Kondo, Yoshiyuki,Suginome, Michinori
, p. 3518 - 3519 (2008/01/01)
An enantioselective silaborative C-C cleavage of meso-methylenecyclopropanes (meso-MCPs) was achieved by using a palladium catalyst bearing a chiral monodentate phosphine ligand. The (R)-2-bis(3,5-dimethylphenyl)phosphino-1,1′-binaphthyl gave the highest
Reductive generation of enolates from enones using elemental hydrogen: Catalytic C-C bond formation under hydrogenative conditions
Jang, Hye-Young,Huddleston, Ryan R.,Krische, Michael J.
, p. 15156 - 15157 (2007/10/03)
Exposure of enones to elemental hydrogen in the presence of a Rh(I) catalyst enables reductive enolate generation, as evidenced by electrophilic trapping of the enolate by appendant and exogenous aldehyde partners. The significance of these findings resides in the ability to regioselectivity generate and transform transition metal enolates under catalytic conditions that circumvent formation of stoichiometric byproducts. Copyright
Chiral orthoesters in organic synthesis: Novel reagents for the enantioselective acylation of silylenolethers
Longobardo, Luigi,Mobbili, Giovanna,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 1299 - 1316 (2007/10/02)
Dialkyl trans-2-alkoxy-2-alkyl-1,3-dioxolan-4,5-dicarboxylates and the corresponding N,N,N,N-tetramethyl-4,5-diamides have been prepared respectively from dialkyl tartrates or tartaric acid diamides. They smoothly reacted with silylenolethers in the prese
Formation of β-Hydroxyketones from α,β-Epoxyketones by Photoinduced Single Electron Transfer Reactions
Cossy, J.,Bouzide, A.,Ibhi, S.,Aclinou, P.
, p. 7775 - 7782 (2007/10/02)
Irradiation of α,β-epoxyketones in acetonitrile at 254 nm in the presence of triethylamine afforded β-hydroxyketones in good to moderate yields. Key words: α,β-epoxyketones, β-hydroxyketones, radical, photochemistry.
REDUCTION OF DELTA 2-ISOXAZOLINES. PART 3: RANEY-NICKEL CATALYZED FORMATION OF beta -HYDROXY KETONES.
Curran
, p. 5826 - 5833 (2007/10/02)
The importance of the beta -hydroxy ketone moiety has led to the development of a wide variety of aldol type methodologies for its construction. A conceptually new approach to these 'aldol adducts' is presented on the basis of left bracket 3 plus 2 right bracket dipolar cycloaddition of in situ generated nitrile oxides and olefins followed by reduction of the resulting DELTA **2-isoxazolines. This approach provides a nice complement of the aldol type reaction. Optimum conditions for the transformation of DELTA **2-isoxazolines to beta -hydroxy ketones use Raney-nickel catalyst, boric acid, 5/1 MeOH/H//2O, and hydrogen gas. Under these mild conditions, 3-methyl-5-n-butyl- DELTA **2-isoxazoline is transformed to 4-hydroxy-2-octanone in high yield. Thus 'directed aldol' type adducts are readily available by selection of the appropriate olefin and nitrile oxide precursor (usually the 1 degree nitro compound).
