186182-40-1Relevant academic research and scientific papers
Room temperature asymmetric Pd-catalyzed methoxycarbonylation of norbornene: Highly selective catalysis and HP-NMR studies
Blanco, Carolina,Godard, Cyril,Zangrando, Ennio,Ruiz, Aurora,Claver, Carmen
experimental part, p. 6980 - 6991 (2012/07/14)
Palladium complexes bearing monodentate and bidentate phosphine ligands (1-7) were synthesised and used as catalyst precursors in the methoxycarbonylation of norbornene. The catalytic systems bearing ligands 1, 3 and 4 afforded excellent conversions (>99%) and selectivity of the ester (>99%). NMR investigations showed that using complex 1a as the precursor resulted in the protonated phosphine, 1-H+, being formed under catalytic conditions and thus the addition of acid is not required for the activation of this system since the reaction involving the precursor with methanol under CO pressure produces 2 equivalents of HCl and leads to the formation of the active species. The protonation of ligand 4 under methoxycarbonylation conditions was also observed and the diprotonated diphosphine was isolated and characterised. This compound was tested as a ligand and acid source in a catalysis and provided excellent conversion and high selectivity to the ester.
Unprecedent chemo- and stereoselective palladium-catalysed methoxycarbonylation of norbornene
Blanco, Carolina,Ruiz, Aurora,Godard, Cyril,Fleury-Bregeot, Nicolas,Marinetti, Angela,Claver, Carmen
experimental part, p. 1813 - 1816 (2011/02/26)
Catalytic systems able to control chemoand stereoselectivity have been tested in the palladium-catalysed methoxycarbonylation of norbornene. An enantioselectivity of up to 40% was obtained.
Asymmetric hydroesterification of norbornene by chiral non-chelate biphosphine palladium complexes
Zhou, Hongying,Lu, Shijie,Hou, Jingguo,Chen, Jing,Fu, Hongxiang,Wang, Hanqing
, p. 339 - 340 (2007/10/03)
Asymmetric induction up to 92.2% has been obtained in the hydroesterification of norbornene with carbon monoxide and alcohols in the presence of Pd(OAc)2, 1,4:3,6-dianhydro-2,5-dideoxy-2,5-bis(diphenylphosphino)-L-iditol and p-toluene-sulfonic acid.
Ueber die Reaktion 1,2-disubstituierter Norbornane mit Dinatriumtetracarbonylferrat(-II)
Camenzind, Hugo,Voegeli, Ulrich Christian,Keese, Reinhart
, p. 168 - 176 (2007/10/02)
Reductive elimination at 1,2exo-diiodonorbornane (6) was induced by Collman's reagent.Surprisingly, 1,2endo-diiodonorbornane (9) and 1-iodo-2endo-trifluoromethylsulfonyloxy-norbornane (10b) lead only to reactions of the substituent in 2-position.Mechanistic aspects are related to the reactions of monosubstituted iodonorbornanes with Collman's reagent.
KINETIC RESOLUTION OF RACEMIC GRIGNARD REAGENTS BY NICKEL-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING
Hayashi, Tamio,Kanehira, Koichi,Hioki, Tsuyoshi,Kumada, Makoto
, p. 137 - 140 (2007/10/02)
Racemic Grignard reagents, 2-phenylpropylmagnesium chloride and 2-norbornylmagnesium chloride were kinetically resolved by asymmetric cross-coupling with vinyl bromides in the presence of chiral phosphine-nickel catalysts to give optically active coupling products (ca. 37percent ee) and carboxylic acids after carbonation with carbon dioxide.
