Advantageous asymmetric ketone reduction with a competitive hydrogenation/transfer hydrogenation system using chiral bifunctional iridium catalysts

RSC Advances ◽  
2014 ◽  
Vol 4 (105) ◽  
pp. 61001-61004 ◽  
Author(s):  
Junki Moritani ◽  
Yoshihito Kayaki ◽  
Takao Ikariya
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Ketone Reduction ◽  
Iridium Catalysts ◽  
Competitive Hydrogenation ◽  
Ketone Hydrogenation

Asymmetric ketone hydrogenation with bifunctional amidoiridium complexes in methanol or ethanol proceeds competitively with asymmetric transfer hydrogenation, in which the pressurised hydrogen can suppress involuntary racemisation of the product.

scholarly journals From imine to amine: an unexpected left turn. Cis-β iron(ii) PNNP′ precatalysts for the asymmetric transfer hydrogenation of acetophenone

2017 ◽  
Vol 8 (9) ◽  
pp. 6531-6541 ◽  
Author(s):  
Karl Z. Demmans ◽  
Chris S. G. Seo ◽  
Alan J. Lough ◽  
Robert H. Morris
Keyword(s):  
Iron Catalyst ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Catalyst Structure ◽  
Ketone Reduction ◽  
Left Turn ◽  
Complete Reversal

A slight change in the iron catalyst structure (amine arm with PEt2 to imine arm with PPh2) results in a complete reversal of the enantioselectivity toward ketone reduction.

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

Dendritic catalysts for asymmetric transfer hydrogenation based (1S,2R)-norephedrine derived ligands

2003 ◽  
Vol 14 (16) ◽  
pp. 2481-2485 ◽  
Author(s):  
Pei Nian Liu ◽  
Ying Chun Chen ◽  
Xue Qiang Li ◽  
Yong Qiang Tu ◽  
Jin Gen Deng
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation

An Efficient Ir(III) Catalyst for the Asymmetric Transfer Hydrogenation of Ketones in Neat Water

Synlett ◽  
2006 ◽  
Vol 2006 (08) ◽  
pp. 1155-1160 ◽  
Author(s):  
Jianliang Xiao ◽  
Xiaohong Li ◽  
John Blacker ◽  
Ian Houson ◽  
Xiaofeng Wu
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Neat Water
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