31042-01-0Relevant academic research and scientific papers
Reductive aldol-type reaction of α,β-unsaturated esters with aldehydes or ketones in the presence of Rh catalyst and Et2Zn
Sato, Kazuyuki,Isoda, Motoyuki,Tokura, Yoriko,Omura, Keiko,Tarui, Atsushi,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
, p. 5913 - 5915 (2013/10/21)
The reaction of RhCl(PPh3)3 with Et2Zn easily generated a rhodium-hydride complex (Rh-H) that added to α,β-unsaturated esters to form rhodium enolate complexes by formal 1,4-reduction. These rhodium enolates gave the corre
Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters
Durandetti, Muriel,Gosmini, Corinne,Périchon, Jacques
, p. 1146 - 1153 (2007/10/03)
Coupling reactions of α-chloroesters with aryl halides (α-arylation) or carbonyl compounds (Reformatsky) using nickel catalyst allow, under mild conditions, the preparation of various functionalized aryl propionic acid derivatives or β-hydroxyesters. In the synthesis of aryl propionic acid derivatives, the process is efficient with aryl halides bearing either electron-withdrawing or electron-donating groups.
Iron-catalysed Reformatsky-type reactions
Durandetti, Muriel,Perichon, Jacques
, p. 1542 - 1548 (2007/10/03)
A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloro
Iron-mediated electrochemical reaction of α-chloroesters with carbonyl compounds
Durandetti, Muriel,Meignein, Clothilde,Perichon, Jacques
, p. 317 - 320 (2007/10/03)
(Matrix presented) Reformatsky-type reactions have been performed efficiently using an electroassisted iron-complex catalysis. Valuable product such as β-hydroxyesters, ketones or nitriles are thus prepared with high yields.
The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1,3-diols
Christlieb,Davies,Eames,Hooley,Warren
, p. 2983 - 2996 (2007/10/03)
A solution of 2-methyl-3-[1-(phenylsulfanyl)cyclohexyl]propane-1,3-diol 1 in toluene treated with triphenyl-phosphine, Ziram 2 and DEAD, gave 3-methyl-2-[1-(phenylsulfanyl)cyclohexyl]oxetane 3 in 85% yield. A mechanistic study has been undertaken, optimal conditions have been found and the range of substrates for which the reaction is useful has been explored. We include the results of an X-ray study which shows that compound 33 (the oxidation product of diol 1) is a sulfone rather than a sulfoxide as previously reported.
Electrochemical activation of zinc in the coupling reaction of α-bromoesters with carbonyl compounds
Rollin, Y.,Gebehenne, C.,Derien, S.,Dunach, E.,Perichon, J.
, p. 9 - 14 (2007/10/02)
The Reformatsky reaction has been examined using a mild and effective method of electrochemical zinc activation, based on the cathodic reduction of a catalytic amount of zing bromide in acetonitrile.
Metal Exchange between an Electrogenerated Organonickel Species and Zinc Halide: Application to an Electrochemical, Nickel-Catalyzed Reformatsky Reaction
Conan, Annie,Sibille, Soline,Perichon, Jacques
, p. 2018 - 2024 (2007/10/02)
The mechanism of the electroreductive coupling of α-chloro esters or α-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques.The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the α-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent.The electrosynthesis of various β-hydroxy esters, β-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.
