Literature DB >> 29701289

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

Kevin J Schwarz1, Colin M Pearson1, Gabriel A Cintron-Rosado2, Peng Liu2, Thomas N Snaddon1.   

Abstract

Cooperative catalysis enables the direct enantioselective α-allylation of linear prochiral esters with 2-substituted allyl electrophiles. Critical to the successful development of the method was the recognition that metal-centered reactivity and the source of enantiocontrol are independent. This feature is unique to simultaneous catalysis events and permits logical tuning of the supporting ligands without compromising enantioselectivity.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis bases; allylation; ammonium enolates; asymmetric catalysis; palladium

Mesh：

Substances：

Year:  2018        PMID： 29701289      PMCID： PMC6038818          DOI： 10.1002/anie.201803277

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


  36 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Organocatalytic Lewis base functionalisation of carboxylic acids, esters and anhydrides via C1-ammonium or azolium enolates.

Authors:  Louis C Morrill; Andrew D Smith
Journal:  Chem Soc Rev       Date:  2014-09-07       Impact factor: 54.564

3.  Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes.

Authors:  Jin Song; Zi-Jing Zhang; Liu-Zhu Gong
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-31       Impact factor: 15.336

Review 4.  Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis.

Authors:  Samson Afewerki; Armando Córdova
Journal:  Chem Rev       Date:  2016-10-10       Impact factor: 60.622

5.  Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  ACS Catal       Date:  2016-08-17       Impact factor: 13.084

6.  Allylic substitution versus Suzuki cross-coupling: capitalizing on chemoselectivity with bifunctional substrates.

Authors:  Mahmud M Hussain; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-01       Impact factor: 15.336

7.  Benzotetramisole-catalyzed dynamic kinetic resolution of azlactones.

Authors:  Xing Yang; Guojian Lu; Vladimir B Birman
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

8.  Uniting C1-Ammonium Enolates and Transition Metal Electrophiles via Cooperative Catalysis: The Direct Asymmetric α-Allylation of Aryl Acetic Acid Esters.

Authors:  Kevin J Schwarz; Jessica L Amos; J Cullen Klein; Dung T Do; Thomas N Snaddon
Journal:  J Am Chem Soc       Date:  2016-04-18       Impact factor: 15.419

9.  Asymmetric organocatalysis combined with metal catalysis: concept, proof of concept, and beyond.

Authors:  Dian-Feng Chen; Zhi-Yong Han; Xiao-Le Zhou; Liu-Zhu Gong
Journal:  Acc Chem Res       Date:  2014-06-09       Impact factor: 22.384

10.  Enantioselective nucleophile-catalyzed synthesis of tertiary alkyl fluorides via the α-fluorination of ketenes: synthetic and mechanistic studies.

Authors:  Sarah Yunmi Lee; Stefan Neufeind; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-06-12       Impact factor: 15.419
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  6 in total

1.  Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles.

Authors:  Kevin J Schwarz; Chao Yang; James W B Fyfe; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-20       Impact factor: 15.336

2.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

Review 3.  Recent progress in asymmetric synergistic catalysis - the judicious combination of selected chiral aminocatalysts with achiral metal catalysts.

Authors:  Christian D-T Nielsen; Joshua D Linfoot; Alexander F Williams; Alan C Spivey
Journal:  Org Biomol Chem       Date:  2022-04-06       Impact factor: 3.890

4.  Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.

Authors:  Jacqueline Bitai; Alastair J Nimmo; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-28       Impact factor: 16.823

5.  A Desilylative Approach to Alkyl Substituted C(1)-Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions.

Authors:  Yihong Wang; Claire M Young; Honglei Liu; Will C Hartley; Max Wienhold; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

6.  Exploring the Scope of Tandem Palladium and Isothiourea Relay Catalysis for the Synthesis of α-Amino Acid Derivatives.

Authors:  Jacqueline Bitai; Alexandra M Z Slawin; David B Cordes; Andrew D Smith
Journal:  Molecules       Date:  2020-05-25       Impact factor: 4.411
  6 in total

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