Literature DB >> 15352183

Towards perfect catalytic asymmetric synthesis: dual activation of the electrophile and the nucleophile.

Jun-An Ma1, Dominique Cahard.   

Abstract

The design and development of new high-performance catalysts for applications in asymmetric catalytic reactions is of ongoing interest in organic chemistry. The combination of a Lewis acid and a Lewis base working in concert is now considered state of the art in stereoselective syntheses. The synergistic activation by two or more reactive centers allows high reaction rates and excellent transfer of stereochemical information. Despite the self-quenching reaction between Lewis acids and Lewis bases that might lead to an inactive catalyst, considerable effort has been directed towards the development of the dual-activation concept. The ultimate goal is to mimic nature by the discovery of catalytic systems analogous to enzymatic processes that involve metal-ion cocatalysts. With this aim, the dual activation concept greatly broadens the range of artificial catalysts. The most efficient catalytic systems are reviewed, and the mechanisms of action are discussed.

Entities:  

Year:  2004        PMID: 15352183     DOI: 10.1002/anie.200300635

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  17 in total

1.  Cooperative N-heterocyclic carbene/Lewis acid catalysis for highly stereoselective annulation reactions with homoenolates.

Authors:  Benoit Cardinal-David; Dustin E A Raup; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

2.  Scaffolding Catalysis: Expanding the Repertoire of Bifunctional Catalysts.

Authors:  Kian L Tan; Xixi Sun; Amanda D Worthy
Journal:  Synlett       Date:  2012-02-01       Impact factor: 2.454

3.  Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.

Authors:  Kevin J Schwarz; Colin M Pearson; Gabriel A Cintron-Rosado; Peng Liu; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-18       Impact factor: 15.336

4.  Bifunctional asymmetric catalysis: amplification of Brønsted basicity can orthogonally increase the reactivity of a chiral Brønsted acid.

Authors:  Tyler A Davis; Jeremy C Wilt; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

5.  Asymmetric bisboranes as bidentate catalysts for carbonyl substrates.

Authors:  Andrew A Rodriguez; Carrie Zhao; Kenneth J Shea
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

6.  Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates.

Authors:  Gardner S Creech; Xue-Feng Zhu; Branden Fonovic; Travis Dudding; Ohyun Kwon
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

7.  Dramatic improvement in catalyst loadings and molar ratios of coupling partners for Ni/Cr-mediated coupling reactions: heterobimetallic catalysts.

Authors:  Xiang Liu; James A Henderson; Takeo Sasaki; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

8.  Stereogenic-at-metal Zn- and Al-based N-heterocyclic carbene (NHC) complexes as bifunctional catalysts in Cu-free enantioselective allylic alkylations.

Authors:  Yunmi Lee; Bo Li; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

9.  Kinetic evidence of an apparent negative activation enthalpy in an organocatalytic process.

Authors:  Xiao Han; Richmond Lee; Tao Chen; Jie Luo; Yixin Lu; Kuo-Wei Huang
Journal:  Sci Rep       Date:  2013       Impact factor: 4.379

10.  Trisubstituted 2-trifluoromethyl pyrrolidines via catalytic asymmetric Michael addition/reductive cyclization.

Authors:  Michael T Corbett; Qihai Xu; Jeffrey S Johnson
Journal:  Org Lett       Date:  2014-04-18       Impact factor: 6.005

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