Enantioselective hydrogenation of N-heteroaromatics catalyzed by chiral diphosphine modified binaphthyl palladium nanoparticles

2017 ◽  
Vol 7 (23) ◽  
pp. 5515-5520 ◽  
Author(s):  
Yun-Tao Xia ◽  
Jing Ma ◽  
Xiao-Dong Wang ◽  
Lei Yang ◽  
Lei Wu
Keyword(s):  
Palladium Nanoparticles ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation

The first application of binaphthyl-stabilized palladium nanoparticles (Bin-PdNPs) with chiral modifiers in asymmetric hydrogenation of N-heteroaromatics is revealed.

Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand

Synlett ◽  
2020 ◽  
Vol 31 (03) ◽  
pp. 285-289 ◽  
Author(s):  
Fei Ling ◽  
Jiachen Chen ◽  
Sanfei Nian ◽  
Huacui Hou ◽  
Xiao Yi ◽  
...  
Keyword(s):  
Functional Group ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Tridentate Ligand ◽  
Easy Access ◽  
Tridentate Ligands

A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable ‘side arm’ groups have been established, enabling the inexpensive base-promoted asymmetric hydrogenation of simple ketones with outstanding activities (up to 8200 TON) and good enantioselectivities (up to 88.5% ee). This protocol features wide substrate scope and functional group tolerance, thereby providing easy access to a key intermediate of crizotinib.

Rhodium/bisphosphine-thiourea-catalyzed enantioselective hydrogenation of α,β-unsaturated N-acylpyrazoles

2016 ◽  
Vol 52 (78) ◽  
pp. 11677-11680 ◽  
Author(s):  
Pan Li ◽  
Xinquan Hu ◽  
Xiu-Qin Dong ◽  
Xumu Zhang
Keyword(s):  
Catalytic System ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
High Yields

We successfully extended our Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system to asymmetric hydrogenation of α,β-unsaturated N-acylpyrazoles affording products with high yields and excellent enantioselectivities (up to 97% yield, 99% ee).

Metal–ligand bifunctional catalysis for asymmetric hydrogenation

2005 ◽  
Vol 363 (1829) ◽  
pp. 901-912 ◽  
Author(s):  
Ryoji Noyori ◽  
Christian A Sandoval ◽  
Kilian Muñiz ◽  
Takeshi Ohkuma
Keyword(s):  
Asymmetric Catalysis ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Molecular Surface ◽  
Metal Alkoxide ◽  
Bifunctional Catalysis ◽  
Bifunctional Mechanism ◽  
Prochiral Ketones ◽  
Membered Transition State ◽  
Metal Ligand

Chiral diphosphine/1,2-diamine–Ru(II) complexes catalyse the rapid, productive and enantioselective hydrogenation of simple ketones. The carbonyl-selective hydrogenation takes place via a non-classical metal–ligand bifunctional mechanism. The reduction of the C=O function occurs in the outer coordination sphere of an 18e trans -RuH 2 (diphosphine)(diamine) complex without interaction between the unsaturated moiety and the metallic centre. The Ru atom donates a hydride and the NH 2 ligand delivers a proton through a pericyclic six-membered transition state, directly giving an alcoholic product without metal alkoxide formation. The enantiofaces of prochiral ketones are differentiated on the chiral molecular surface of the saturated RuH 2 species. This asymmetric catalysis manifests the significance of ‘kinetic’ supramolecular chemistry.

Chiral phosphine-phosphoramidite ligands for highly enantioselective hydrogenation of N-arylimines

RSC Advances ◽  
2015 ◽  
Vol 5 (18) ◽  
pp. 13702-13708 ◽  
Author(s):  
Qing Li ◽  
Chuan-Jin Hou ◽  
Xiao-Ning Liu ◽  
De-Zhi Huang ◽  
Yan-Jun Liu ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
High Turnover

The asymmetric hydrogenation of N-arylimines with the chiral phosphine-phosphoramidite ligand, (Sc,Sa)-PEAPhos 2b, has been developed, in which high turnover numbers and excellent enantioselectivity were achieved.

Enantioselective Hydrogenation of Cyclic Tetrasubstituted-Olefinic Dehydroamino Acid Derivatives

2021 ◽  
Author(s):  
Feng Wan ◽  
Nan Wang ◽  
Yuxin Zhu ◽  
Chuyan Tang ◽  
Jerome P Claverie ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Chiral Centers ◽  
Dehydroamino Acid

Efficient asymmetric hydrogenation of cyclic tetrasubstituted-olefinic dehydroamino acid derivatives have been achieved with a Rh-ArcPhos catalyst, affording a series of α-acylamino-β-alkyl tetrahydropyranones with two contiguous chiral centers in up to...

Iridium-catalyzed asymmetric hydrogenation of dibenzo[b,f][1,4]thiazepines

2013 ◽  
Vol 85 (4) ◽  
pp. 843-849 ◽  
Author(s):  
Ran-Ning Guo ◽  
Kai Gao ◽  
Zhi-Shi Ye ◽  
Lei Shi ◽  
Yanqin Li ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Optically Active ◽  
Efficient Access

Highly enantioselective hydrogenation of substituted dibenzo[b,f][1,4]thiazepines was achieved with up to 96 % ee (enantiomeric excess) using [Ir(COD)Cl]2/(R)-SynPhos complex as catalyst in the presence of iodine. This method provides an efficient access to optically active 11-substituted-10,11-dihydrodibenzo[b,f][1,4]thiazepines.

Rhodium-catalyzed enantioselective hydrogenation of α-amino acrylonitriles: an efficient approach to synthesizing chiral α-amino nitriles

2017 ◽  
Vol 53 (7) ◽  
pp. 1313-1316 ◽  
Author(s):  
Xiuxiu Li ◽  
Cai You ◽  
Yusheng Yang ◽  
Fangyuan Wang ◽  
Shuailong Li ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Efficient Approach

An efficient asymmetric hydrogenation of α-amino acrylonitriles has been achieved, affording chiral α-amino nitriles in excellent yields and enantioselectivities regardless of the cis–trans configuration of α-amino acrylonitriles.

Synthesis of polymers containing chiral 1,2-diamine derivatives and their application to asymmetric reactions

2007 ◽  
Vol 79 (9) ◽  
pp. 1471-1479 ◽  
Author(s):  
Shinichi Itsuno ◽  
Miyuki Takahashi ◽  
Yukihiro Arakawa ◽  
Naoki Haraguchi
Keyword(s):  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Transfer Hydrogenation ◽  
Hydrogenation Catalyst ◽  
Polymer Support ◽  
Secondary Alcohols ◽  
Aromatic Ketones ◽  
Neat Water ◽  
Polymeric Catalyst ◽  
High Level

Polymer-supported chiral 1,2-diamine derivatives have been prepared. The polymers containing free 1,2-diamine moiety were applied to enantioselective hydrogenation catalyst by combination with RuCl2-BINAP complex. Asymmetric hydrogenation of aromatic ketones was performed by means of the polymeric catalyst derived from these polymers to give the chiral secondary alcohols with high ee in quantitative conversion. The polymers containing 1,2-diamine monosulfonamide were applied to enantioselective transfer hydrogenation catalyst by combination with RuCl2-p-cymene complex. Asymmetric transfer hydrogenation of aromatic ketones was performed by means of the polymeric catalyst to afford the chiral secondary alcohols. A high level of enantioselectivities up to 99 % ee was attained in neat water by using the polymeric catalyst prepared from quaternary ammonium salt-type polymer support.

In situ Chiral Modification of Nickel Catalysts for Enantioselective Hydrogenation of Methyl Acetoacetate

2005 ◽  
Vol 70 (10) ◽  
pp. 1642-1652 ◽  
Author(s):  
Lukáš Bartek ◽  
Petr Klusoň ◽  
Libor Červený
Keyword(s):  
Raney Nickel ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Nickel Catalysts ◽  
Methyl Acetoacetate ◽  
Repeated Use ◽  
Series Of Experiments ◽  
Chiral Modification ◽  
Characteristic Features

Chiral modifications of SiO2-supported and Raney nickel catalysts were studied. The catalysts were employed in asymmetric hydrogenation of methyl acetoacetate (MAA) to (R)- and (S)-enantiomers of methyl 3-hydroxybutanoate. The effects of modification parameters such as type and concentration of modifier; presence of a co-modifier and other additives, pH of modification solution on the enantioselectivity of MAA hydrogenation were discussed. Characteristic features of the in situ modification of Ni/SiO2 were also evaluated and the results obtained were compared with the conventional (premodification) approach. Parameters for the conventional and in situ methods were optimised in a series of experiments for both types of catalysts. The in situ modified Ni/SiO2 was found specifically suitable for repeated use due to virtually no decrease in selectivity and activity.

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