Literature DB >> 24729943

Comparison Of Asymmetric Hydrogenations Of Unsaturated- Carboxylic Acids And -Esters.

Sakunchai Khumsubdee1, Kevin Burgess1.   

Abstract

As methodology development matures it can be difficult to discern the most effective ways of performing certain transformations from the rest. This review summarizes the most important contributions leading to asymmetric hydrogenations of simple unsaturated-acid and ester substrates, with the objective of highlighting at least the best types of catalysts for each. Achievements in the area are described and these reveal situations where further efforts should be worthwhile, and ones where more research is only likely to give diminishing returns. In general, our conclusions are that the most useful types of catalysts for unsaturated-acids and -esters tend to be somewhat different, simple substrates have been studied extensively, and the field is poised to address more complex reactions. These could be ones involving alternative, particularly cyclic, structures, chemoselectivity issues, and more complex substrate stereochemistries.

Entities:  

Keywords:  alkene-acids; alkene-esters; homogeneous; hydrogenations; stereoselective

Year:  2013        PMID: 24729943      PMCID: PMC3982802          DOI: 10.1021/cs3007389

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  41 in total

1.  A new principle in combinatorial asymmetric transition-metal catalysis: mixtures of chiral monodentate P ligands.

Authors:  Manfred T Reetz; Thorsten Sell; Andreas Meiswinkel; Gerlinde Mehler
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-17       Impact factor: 15.336

2.  Iridium catalysts with bicyclic pyridine-phosphinite ligands: asymmetric hydrogenation of olefins and furan derivatives.

Authors:  Stefan Kaiser; Sebastian P Smidt; Andreas Pfaltz
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-04       Impact factor: 15.336

3.  Electronic effects steer the mechanism of asymmetric hydrogenations of unfunctionalized aryl-substituted alkenes.

Authors:  Yubo Fan; Xiuhua Cui; Kevin Burgess; Michael B Hall
Journal:  J Am Chem Soc       Date:  2004-12-29       Impact factor: 15.419

4.  Proline-based P,O ligand/iridium complexes as highly selective catalysts: asymmetric hydrogenation of trisubstituted alkenes.

Authors:  Denise Rageot; David H Woodmansee; Benoît Pugin; Andreas Pfaltz
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-31       Impact factor: 15.336

5.  Pyranoside phosphite-oxazoline ligands for the highly versatile and enantioselective ir-catalyzed hydrogenation of minimally functionalized olefins. A combined theoretical and experimental study.

Authors:  Javier Mazuela; Per-Ola Norrby; Pher G Andersson; Oscar Pàmies; Montserrat Diéguez
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

6.  Recent advances in iridium-catalyzed asymmetric hydrogenation: new catalysts, substrates and applications in total synthesis.

Authors:  Adnan Ganić; Denise Rageot; Lars Tröndlin; Andreas Pfaltz
Journal:  Chimia (Aarau)       Date:  2012       Impact factor: 1.509

7.  Enantioselective Rh-catalyzed hydrogenation of 3-aryl-4-phosphonobutenoates with a P-stereogenic BoPhoz-type ligand.

Authors:  Zheng-Chao Duan; Xiang-Ping Hu; Cheng Zhang; Zhuo Zheng
Journal:  J Org Chem       Date:  2010-11-09       Impact factor: 4.354

8.  Synthesis of a new class of conformationally rigid phosphino-oxazolines: highly enantioselective ligands for Ir-catalyzed asymmetric hydrogenation.

Authors:  Duan Liu; Wenjun Tang; Xumu Zhang
Journal:  Org Lett       Date:  2004-02-19       Impact factor: 6.005

9.  Chiral diphosphine and monodentate phosphorus ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions.

Authors:  Jian-Hua Xie; Qi-Lin Zhou
Journal:  Acc Chem Res       Date:  2008-03-01       Impact factor: 22.384

10.  New mechanistic insights into the iridium-phosphanooxazoline-catalyzed hydrogenation of unfunctionalized olefins: a DFT and kinetic study.

Authors:  Peter Brandt; Christian Hedberg; Pher G Andersson
Journal:  Chemistry       Date:  2003-01-03       Impact factor: 5.236

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  8 in total

1.  CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.

Authors:  Achim Link; Yujing Zhou; Stephen L Buchwald
Journal:  Org Lett       Date:  2020-07-06       Impact factor: 6.005

2.  Homo-Roche ester derivatives by asymmetric hydrogenation and organocatalysis.

Authors:  Sakunchai Khumsubdee; Hua Zhou; Kevin Burgess
Journal:  J Org Chem       Date:  2013-11-12       Impact factor: 4.354

3.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

Review 4.  Conjugate addition-enantioselective protonation reactions.

Authors:  James P Phelan; Jonathan A Ellman
Journal:  Beilstein J Org Chem       Date:  2016-06-15       Impact factor: 2.883

5.  Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes.

Authors:  Veronika M Shoba; James M Takacs
Journal:  J Am Chem Soc       Date:  2017-04-17       Impact factor: 15.419

6.  Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids.

Authors:  Shuang Yang; Wen Che; Hui-Ling Wu; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2016-11-15       Impact factor: 9.825

7.  Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination.

Authors:  Zhao Wu; Summer D Laffoon; Kami L Hull
Journal:  Nat Commun       Date:  2018-03-22       Impact factor: 14.919

8.  Catalytic enantioselective addition of organometallics to unprotected carboxylic acids.

Authors:  Xingchen Yan; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2019-07-30       Impact factor: 14.919

  8 in total

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