Catalytic Cycle for the Asymmetric Hydrogenation of Prochiral Ketones to Chiral Alcohols:  Direct Hydride and Proton Transfer from Chiral Catalyststrans-Ru(H)2(diphosphine)(diamine) to Ketones and Direct Addition of Dihydrogen to the Resulting Hydridoamido Complexes

2001 ◽  
Vol 123 (30) ◽  
pp. 7473-7474 ◽  
Author(s):  
Kamaluddin Abdur-Rashid ◽  
Michael Faatz ◽  
Alan J. Lough ◽  
Robert H. Morris
Keyword(s):  
Proton Transfer ◽  
Asymmetric Hydrogenation ◽  
Catalytic Cycle ◽  
Chiral Alcohols ◽  
Direct Addition ◽  
Prochiral Ketones

scholarly journals Broad Scope Synthesis of Ester Precursors of Nonfunctionalized Chiral Alcohols Based on the Asymmetric Hydrogenation of α,β-Dialkyl-, α,β-Diaryl-, and α-Alkyl-β-aryl-vinyl Esters

2017 ◽  
Vol 82 (11) ◽  
pp. 5852-5867 ◽  
Author(s):  
Félix León ◽  
Pedro J. González-Liste ◽  
Sergio E. García-Garrido ◽  
Inmaculada Arribas ◽  
Miguel Rubio ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Chiral Alcohols ◽  
Vinyl Esters ◽  
Broad Scope

scholarly journals Proton Transfer in the Catalytic Cycle of [NiFe] Hydrogenases: Insight from Vibrational Spectroscopy

ACS Catalysis ◽  
2017 ◽  
Vol 7 (4) ◽  
pp. 2471-2485 ◽  
Author(s):  
Philip A. Ash ◽  
Ricardo Hidalgo ◽  
Kylie A. Vincent
Keyword(s):  
Proton Transfer ◽  
Vibrational Spectroscopy ◽  
Catalytic Cycle

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.

Modular DNA-based hybrid catalysts as a toolbox for enantioselective hydration of α,β-unsaturated ketones

2019 ◽  
Vol 17 (9) ◽  
pp. 2548-2553 ◽  
Author(s):  
Ji Hye Yum ◽  
Soyoung Park ◽  
Ryota Hiraga ◽  
Izumi Okamura ◽  
Shunta Notsu ◽  
...  
Keyword(s):  
Double Bond ◽  
Direct Access ◽  
Chiral Alcohols ◽  
Unsaturated Ketones ◽  
Hybrid Catalysts ◽  
Carbon Double Bond ◽  
Direct Addition

The direct addition of water to a carbon–carbon double bond remains a challenge, but such a reaction is essential for the development of efficient catalysts that enable direct access to chiral alcohols.

Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation

2018 ◽  
Vol 20 (4) ◽  
pp. 1110-1113 ◽  
Author(s):  
Sensheng Liu ◽  
Huan Liu ◽  
Haifeng Zhou ◽  
Qixing Liu ◽  
Jinliang Lv
Keyword(s):  
Asymmetric Hydrogenation ◽  
Chiral Alcohols

Recent Advance in Organocatalyzed Asymmetric Reduction of Prochiral Ketones: An Update

Synthesis ◽  
2021 ◽  
Author(s):  
Xu-Long Qin ◽  
Li-Jun Xu ◽  
Fu-She Han
Keyword(s):  
Asymmetric Reduction ◽  
Building Blocks ◽  
Short Review ◽  
Chiral Alcohols ◽  
Comprehensive Overview ◽  
Synthetic Intermediates ◽  
Prochiral Ketones ◽  
Catalyzed Reactions ◽  
Enzyme Catalyzed Reactions ◽  
Easy Operation

Chiral alcohols are important synthetic intermediates or building blocks for the diverse synthesis of drugs, agrochemicals, and natural products. Asymmetric reduction of prochiral ketones has been the most popularly investigated method for accessing chiral alcohols. In this regard, the organocatalyzed asymmetric reduction as a complementary of transition-metal- and enzyme-catalyzed reactions have attracted tremendous interest in the past decades due to the nature of metal-free and easy operation, as well as, principly, the ease of recovery and reuse of catalysts. Following up a comprehensive overview on organocatalyzed asymmetric reduction of prochiral ketones in early 2018, this short review is intended to summarize the recent progress in this area from the beginning of the year 2018 to the end of Aug. 2021.

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