Literature DB >> 15034179

Toward efficient asymmetric hydrogenation: architectural and functional engineering of chiral molecular catalysts.

Ryoji Noyori1, Masato Kitamura, Takeshi Ohkuma.   

Abstract

Asymmetric hydrogenation uses inexpensive, clean hydrogen gas and a very small amount of a chiral molecular catalyst, providing the most powerful way to produce a wide array of enantio-enriched compounds in a large quantity without forming any waste. The recent revolutionary advances in this field have entirely changed the synthetic approach to producing performance chemicals that require a high degree of structural precision. The means of developing efficient asymmetric hydrogenations is discussed from a mechanistic point of view.

Entities:  

Year:  2004        PMID: 15034179      PMCID: PMC397385          DOI: 10.1073/pnas.0307928100

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  12 in total

1.  Asymmetric catalysis: science and opportunities (Nobel lecture).

Authors:  Ryoji Noyori
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336

2.  Chiral metal complexes as discriminating molecular catalysts.

Authors:  R Noyori
Journal:  Science       Date:  1990-06-08       Impact factor: 47.728

3.  Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones.

Authors:  Ryoji Noyori; Takeshi Ohkuma
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

Review 4.  Modular phospholane ligands in asymmetric catalysis.

Authors:  M J Burk
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

5.  Selective hydrogenation of benzophenones to benzhydrols. Asymmetric synthesis of unsymmetrical diarylmethanols

Authors: 
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

6.  General asymmetric hydrogenation of hetero-aromatic ketones

Authors: 
Journal:  Org Lett       Date:  2000-06-15       Impact factor: 6.005

7.  Mechanism of asymmetric hydrogenation of alpha-(acylamino)acrylic esters catalyzed by BINAP-ruthenium(II) diacetate.

Authors:  Masato Kitamura; Masaki Tsukamoto; Yuhki Bessho; Masahiro Yoshimura; Uwe Kobs; Michael Widhalm; Ryoji Noyori
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

8.  trans-RuH(eta1-BH4)(binap)(1,2-diamine): a catalyst for asymmetric hydrogenation of simple ketones under base-free conditions.

Authors:  Takeshi Ohkuma; Masatoshi Koizumi; Kilian Muñiz; Gerhard Hilt; Chizuko Kabuto; Ryoji Noyori
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

9.  Halide effects in transition metal catalysis.

Authors:  Keith Fagnou; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2002-01-04       Impact factor: 15.336

10.  Mechanism of asymmetric hydrogenation of ketones catalyzed by BINAP/1,2-diamine-rutheniumII complexes.

Authors:  Christian A Sandoval; Takeshi Ohkuma; Kilian Muñiz; Ryoji Noyori
Journal:  J Am Chem Soc       Date:  2003-11-05       Impact factor: 15.419

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  15 in total

Review 1.  Natural products as inspiration for the development of asymmetric catalysis.

Authors:  Justin T Mohr; Michael R Krout; Brian M Stoltz
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

2.  Palladium-catalyzed asymmetric ring expansion of allenylcyclobutanols: an asymmetric Wagner-Meerwein shift.

Authors:  Barry M Trost; Jia Xie
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

3.  Synthesis of Ruthenium Boryl Analogues of the Shvo Metal-Ligand Bifunctional Catalyst.

Authors:  Liza Koren-Selfridge; Ian P Query; Joel A Hanson; Nicholas A Isley; Ilia A Guzei; Timothy B Clark
Journal:  Organometallics       Date:  2010       Impact factor: 3.876

Review 4.  Enatiomerically pure hydroxycarboxylic acids: current approaches and future perspectives.

Authors:  Qun Ren; Katinka Ruth; Linda Thöny-Meyer; Manfred Zinn
Journal:  Appl Microbiol Biotechnol       Date:  2010-06       Impact factor: 4.813

5.  Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.

Authors:  Liqin Qiu; Mahavir Prashad; Bin Hu; Kapa Prasad; Oljan Repic; Thomas J Blacklock; Fuk Yee Kwong; Stanton H L Kok; Hang Wai Lee; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2007-10-17       Impact factor: 11.205

6.  Cyclopentadienone iron alcohol complexes: synthesis, reactivity, and implications for the mechanism of iron-catalyzed hydrogenation of aldehydes.

Authors:  Charles P Casey; Hairong Guan
Journal:  J Am Chem Soc       Date:  2009-02-25       Impact factor: 15.419

Review 7.  Asymmetric hydrogenation of ketones: tactics to achieve high reactivity, enantioselectivity, and wide scope.

Authors:  Takeshi Ohkuma
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2010       Impact factor: 3.493

8.  Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis.

Authors:  Patrick D Parker; Xintong Hou; Vy M Dong
Journal:  J Am Chem Soc       Date:  2021-04-23       Impact factor: 16.383

9.  Enzyme-Modified Particles for Selective Biocatalytic Hydrogenation by Hydrogen-Driven NADH Recycling.

Authors:  Holly A Reeve; Lars Lauterbach; Oliver Lenz; Kylie A Vincent
Journal:  ChemCatChem       Date:  2015-10-28       Impact factor: 5.686

10.  Exploring the full catalytic cycle of rhodium(i)-BINAP-catalysed isomerisation of allylic amines: a graph theory approach for path optimisation.

Authors:  Takayoshi Yoshimura; Satoshi Maeda; Tetsuya Taketsugu; Masaya Sawamura; Keiji Morokuma; Seiji Mori
Journal:  Chem Sci       Date:  2017-05-03       Impact factor: 9.825

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