The Half-sandwich Hydride and 16-Electron Complexes of Rhodium and Iridium Containing (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethylenediamine: Relevant to the Asymmetric Transfer Hydrogenation

1998 ◽  
Vol 27 (12) ◽  
pp. 1201-1202 ◽  
Author(s):  
Kazushi Mashima ◽  
Tomoyuki Abe ◽  
Kazuhide Tani
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Half Sandwich

N,O- vs N,C-Chelation in Half-Sandwich Iridium Complexes: A Dramatic Effect on Enantioselectivity in Asymmetric Transfer Hydrogenation of Ketones

ACS Catalysis ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 8020-8026 ◽  
Author(s):  
Gang Zhou ◽  
Ahmed H. Aboo ◽  
Craig M. Robertson ◽  
Ruixia Liu ◽  
Zhenhua Li ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Iridium Complexes ◽  
Asymmetric Transfer Hydrogenation ◽  
Dramatic Effect ◽  
Half Sandwich

Half-sandwich Ru(η6-C6H6) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

2015 ◽  
Vol 5 (10) ◽  
pp. 4790-4799 ◽  
Author(s):  
Mani Mary Sheeba ◽  
Sankaranarayanan Preethi ◽  
A. Nijamudheen ◽  
Manoharan Muthu Tamizh ◽  
Ayan Datta ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Theoretical Studies ◽  
Asymmetric Transfer Hydrogenation ◽  
Experimental And Theoretical Studies ◽  
Half Sandwich

The efficiency of Ru–benzene complexes towards ATH of ketones was studied.

Half-Sandwich Complexes of Osmium(II) withl-α-Amino Carboxylate Ligands as Asymmetric Transfer Hydrogenation Catalysts. On the Origin of the Enantioselectivity

2012 ◽  
Vol 31 (8) ◽  
pp. 3333-3345 ◽  
Author(s):  
Daniel Carmona ◽  
Fernando J. Lahoz ◽  
Pilar García-Orduña ◽  
Luis A. Oro ◽  
M. Pilar Lamata ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Sandwich Complexes ◽  
Carboxylate Ligands ◽  
Hydrogenation Catalysts ◽  
Half Sandwich

Role of the sulfonamide moiety of Ru(II) half-sandwich complexes in the asymmetric transfer hydrogenation of 3,4-dihydroisoquinolines

2016 ◽  
Vol 118 (1) ◽  
pp. 215-222 ◽  
Author(s):  
Ondřej Matuška ◽  
Jakub Zápal ◽  
Radka Hrdličková ◽  
Miloš Mikoška ◽  
Jan Pecháček ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Sandwich Complexes ◽  
Half Sandwich

scholarly journals New Bifunctional Bis(azairidacycle) with Axial Chirality via Double Cyclometalation of 2,2′-Bis(aminomethyl)-1,1′-binaphthyl

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1165
Author(s):  
Yasuhiro Sato ◽  
Yuichi Kawata ◽  
Shungo Yasui ◽  
Yoshihito Kayaki ◽  
Takao Ikariya
Keyword(s):  
Hydrogen Transfer ◽  
Bond Cleavage ◽  
Enantiomeric Excess ◽  
Transfer Hydrogenation ◽  
Catalyst Precursor ◽  
Asymmetric Catalysts ◽  
Axially Chiral ◽  
Diastereomeric Mixture ◽  
Raney Ni ◽  
Half Sandwich

As a candidate for bifunctional asymmetric catalysts containing a half-sandwich C–N chelating Ir(III) framework (azairidacycle), a dinuclear Ir complex with an axially chiral linkage is newly designed. An expedient synthesis of chiral 2,2′-bis(aminomethyl)-1,1′-binaphthyl (1) from 1,1-bi-2-naphthol (BINOL) was accomplished by a three-step process involving nickel-catalyzed cyanation and subsequent reduction with Raney-Ni and KBH4. The reaction of (S)-1 with an equimolar amount of [IrCl2Cp*]2 (Cp* = η5–C5(CH3)5) in the presence of sodium acetate in acetonitrile at 80 °C gave a diastereomeric mixture of new dinuclear dichloridodiiridium complexes (5) through the double C–H bond cleavage, as confirmed by 1H NMR spectroscopy. A loss of the central chirality on the Ir centers of 5 was demonstrated by treatment with KOC(CH3)3 to generate the corresponding 16e amidoiridium complex 6. The following hydrogen transfer from 2-propanol to 6 provided diastereomers of hydrido(amine)iridium retaining the bis(azairidacycle) architecture. The dinuclear chlorido(amine)iridium 5 can serve as a catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with a substrate to a catalyst ratio of 200 in the presence of KOC(CH3)3 in 2-propanol, leading to (S)-1-phenylethanol with up to an enantiomeric excess (ee) of 67%.

scholarly journals Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl Ketones

Catalysts ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 671
Author(s):  
Chad M. Bernier ◽  
Joseph S. Merola
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantiomeric Excess ◽  
Transfer Hydrogenation ◽  
Acid Catalysts ◽  
Asymmetric Transfer Hydrogenation ◽  
Reaction Conditions ◽  
Chiral Complexes ◽  
Acetophenone Derivatives ◽  
Aryl Ketones

A series of chiral complexes of the form Ir(NHC)2(aa)(H)(X) (NHC = N-heterocyclic carbene, aa = chelated amino acid, X = halide) was synthesized by oxidative addition of -amino acids to iridium(I) bis-NHC compounds and screened for asymmetric transfer hydrogenation of ketones. Following optimization of the reaction conditions, NHC, and amino acid ligands, high enantioselectivity was achieved when employing the Ir(IMe)2(l-Pro)(H)(I) catalyst (IMe = 1,3-dimethylimidazol-2-ylidene), which asymmetrically reduces a range of acetophenone derivatives in up to 95% enantiomeric excess.

Enantioselectivity in the Noyori–Ikariya Asymmetric Transfer Hydrogenation of Ketones

2021 ◽  
Author(s):  
Pavel A. Dub ◽  
Nikolay V. Tkachenko ◽  
Vijyesh K. Vyas ◽  
Martin Wills ◽  
Justin S. Smith ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation
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