Heterogeneous asymmetric reactions

An enantioselective hydrogenation of N-substituted diarylmethanimines under mild conditions has been first realized by using an iridium catalyst with a chiral f-spiroPhos ligand. This method provides an efficient access to the asymmetric synthesis of a variety of chiral diarylmethylamines and their derivatives with excellent enantioselectivities (up to 99.4% ee) and high turnover numbers (TON up to 4000).

Asymmetric hydrogenation

Chiral ligand

10.1021/acs.joc.6b01273

Cite

Citations (39)

Asymmetric hydrogenation of ethyl pyruvate over aqueous dispersed Pt nanoparticles stabilized by a cinchonidine-functionalized β-cyclodextrin

Catalysis Communications (2020)

Sébastien Noël Eleonora Caronia Hervé Bricout Iveta Tichá Stéphane Menuel

Cinchonidine-functionalized β-cyclodextrin was used as stabilizing agent for platinum nanoparticles dispersed in water, but also as chiral modifier for the asymmetric hydrogenation of ethyl pyruvate at 30 °C under 40 bar of hydrogen. This functionalized cyclodextrin allowed getting more stable, more catalytically active and also more enantioselective Pt nanoparticles compared to control catalytic systems. NMR and MALDI-MS analyses clearly showed the reduction of the vinyl group of the cinchonidine graft during the nanoparticles preparation. Under hydrogen pressure, the hydrogenation of the quinolinic moiety was also proven and can be responsible for the difficulties encountered during the recycling study.

Cinchonidine

Asymmetric hydrogenation

Moiety

Platinum nanoparticles

Noyori asymmetric hydrogenation

Ethyl lactate

Transfer hydrogenation

10.1016/j.catcom.2020.106272

Cite

Citations (3)

A novel asymmetric heterogeneous catalytic reaction: hydrogenation of ethyl 2-acetoxyacrylate on cinchonidine modified Pd and Pt catalyst

Reaction Kinetics and Catalysis Letters (2005)

Kornél Szőri György Szőllősi Károly Felföldi Mihály Bartók

Cinchonidine

Asymmetric hydrogenation

10.1007/s11144-005-0203-8

Cite

Citations (12)

Changing from Symmetric to Asymmetric Simply by Immobilizing the Catalyst on Mesoporous Silica Nanoparticle

ChemCatChem (2010)

Yulin Huang Shu Xu Victor S.‐Y. Lin

Immobilization for enantioselectivity: Covalent tethering of a rhodium(I) phosphine complex on the surface of highly ordered mesoporous silica nanoparticles (MSN) gives rise to the RhPMSN/(−)- cinchonidine catalytic system, which gives 50 % ee in the hydrogenation of ethyl pyruvate. In contrast, no enantioselectivity is detected in the hydrogenation of ethyl pyruvate catalyzed by the very similar homogeneous system [RhCl(PPh3)3]/(−)-cinchonidine.

Cinchonidine

Asymmetric hydrogenation

10.1002/cctc.201000294

Cite

Citations (8)

Modeling of the enantioselective hydrogenation of 1-phenyl-1,2-propanedione over Pt/Al2O3 catalyst

Catalysis Today (2001)

Esa Toukoniitty Päivi Mäki‐Arvela Johan Wärnå Tapio Salmi

Cinchonidine

10.1016/s0920-5861(00)00638-6

Cite

Citations (27)