Literature DB >> 27028057

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

Kevin J Schwarz1, Jessica L Amos1, J Cullen Klein1, Dung T Do1, Thomas N Snaddon1.   

Abstract

The direct, catalytic, asymmetric α-functionalization of acyclic esters constitutes a significant challenge in the area of asymmetric catalysis, particularly where the configurational integrity of the products is problematic. Through the unprecedented merger of two independent, yet complementary, catalysis events it has been possible to facilitate the direct asymmetric α-allylation of readily available aryl acetic acid esters. Since enantioselection is determined by the nucleophile, this conceptual approach to cooperative catalysis constitutes a potentially general solution to the direct catalytic asymmetric α-functionalization of acyclic esters.

Entities:  

Year:  2016        PMID: 27028057     DOI: 10.1021/jacs.6b01694

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  23 in total

1.  Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Authors:  Xingyu Jiang; Jason J Beiger; John F Hartwig
Journal:  J Am Chem Soc       Date:  2016-12-22       Impact factor: 15.419

2.  Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.

Authors:  Xingyu Jiang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

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.  Remote Allylation of Unactivated C(sp3)-H Bonds Triggered by Photogenerated Amidyl Radicals.

Authors:  Bin Xu; Uttam K Tambar
Journal:  ACS Catal       Date:  2019-04-16       Impact factor: 13.084

5.  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

6.  Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates.

Authors:  Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2018-08-02       Impact factor: 15.419

7.  Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate.

Authors:  Liyuan Ding; Chunbing Yu; Zhenqiang Zhao; Feifei Li; Jian Zhang; Guofu Zhong
Journal:  J Vis Exp       Date:  2017-06-21       Impact factor: 1.355

8.  CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.

Authors:  Sheng Feng; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-24       Impact factor: 15.419

9.  Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement.

Authors:  Stéphanie S M Spoehrle; Thomas H West; James E Taylor; Alexandra M Z Slawin; Andrew D Smith
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

10.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825

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