Literature DB >> 17563797

Aqueous-phase asymmetric transfer hydrogenation of ketones--a greener approach to chiral alcohols.

Xiaofeng Wu1, Jianliang Xiao.   

Abstract

Asymmetric transfer hydrogenation (ATH) has emerged as a practical, powerful alternative to asymmetric hydrogenation for the production of chiral alcohols, one of the most valuable intermediates in chemical synthesis. In the last a few years, ATH in neat water has proved to be viable, affording chiral alcohols in fast rates, high productivity and high enantioselectivity. The reduction can be carried out with unmodified or tailor-made catalysts by using mild, readily available formate salt as reductant with no organic solvents required, thus providing a simple, economic and green pathway for alcohol production. This Feature Article attempts to present an account of the progress made on aqueous-phase transfer hydrogenation (TH) reactions, with a focus on ATH. The coverage includes a brief background of the chemistry, TH and ATH reactions in water, and the mechanistic aspects of the aqueous-phase reduction.

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Year:  2007        PMID: 17563797     DOI: 10.1039/b618340a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  10 in total

1.  Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.

Authors:  De Run Li; Anyu He; J R Falck
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

2.  Transient Ru-methyl formate intermediates generated with bifunctional transfer hydrogenation catalysts.

Authors:  Richard H Perry; Kristen R Brownell; Konstantin Chingin; Thomas J Cahill; Robert M Waymouth; Richard N Zare
Journal:  Proc Natl Acad Sci U S A       Date:  2012-02-06       Impact factor: 11.205

3.  Designer substrate library for quantitative, predictive modeling of reaction performance.

Authors:  Elizabeth N Bess; Amanda J Bischoff; Matthew S Sigman
Journal:  Proc Natl Acad Sci U S A       Date:  2014-09-29       Impact factor: 11.205

Review 4.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

5.  Coordinating Chiral Ionic Liquids: Design, Synthesis, and Application in Asymmetric Transfer Hydrogenation under Aqueous Conditions.

Authors:  Maria Vasiloiu; Peter Gaertner; Ronald Zirbs; Katharina Bica
Journal:  European J Org Chem       Date:  2015-02-20

6.  Easy To Synthesize, Robust Organo-osmium Asymmetric Transfer Hydrogenation Catalysts.

Authors:  James P C Coverdale; Carlos Sanchez-Cano; Guy J Clarkson; Rina Soni; Martin Wills; Peter J Sadler
Journal:  Chemistry       Date:  2015-04-08       Impact factor: 5.236

7.  Enantio-relay catalysis constructs chiral biaryl alcohols over cascade Suzuki cross-coupling-asymmetric transfer hydrogenation.

Authors:  Dacheng Zhang; Xiaoshuang Gao; Tanyu Cheng; Guohua Liu
Journal:  Sci Rep       Date:  2014-05-28       Impact factor: 4.379

Review 8.  Opportunities offered by chiral η⁶-arene/N-arylsulfonyl-diamine-RuII catalysts in the asymmetric transfer hydrogenation of ketones and imines.

Authors:  Jiří Václavík; Petr Kačer; Marek Kuzma; Libor Cervený
Journal:  Molecules       Date:  2011-06-28       Impact factor: 4.411

9.  pH-Dependent transfer hydrogenation or dihydrogen release catalyzed by a [(η6-arene)RuCl(κ2-N,N-dmobpy)]+ complex: a DFT mechanistic understanding.

Authors:  Chenguang Luo; Longfei Li; Xin Yue; Pengjie Li; Lin Zhang; Zuoyin Yang; Min Pu; Zexing Cao; Ming Lei
Journal:  RSC Adv       Date:  2020-03-11       Impact factor: 4.036

10.  Cyclopentadienone Iron Tricarbonyl Complexes-Catalyzed Hydrogen Transfer in Water.

Authors:  Daouda Ndiaye; Sébastien Coufourier; Mbaye Diagne Mbaye; Sylvain Gaillard; Jean-Luc Renaud
Journal:  Molecules       Date:  2020-01-20       Impact factor: 4.411

  10 in total

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