Literature DB >> 24123891

Formal ring-opening/cross-coupling reactions of 2-pyrones: iron-catalyzed entry into stereodefined dienyl carboxylates.

Chang-Liang Sun1, Alois Fürstner.   

Abstract

Open access: Despite the exceptional level of sophistication in cross-coupling chemistry, reactions of substrates that incorporate the leaving group as an integral part into a heterocyclic scaffold are scarce. The title reaction outlines the utility of this reaction format (see scheme; acac=acetylacetonate), provides a convenient entry into stereodefined diene carboxylates, and adds a new chapter to the field of iron catalysis.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cross-coupling; dienes; heterocycles; iron; natural products

Year:  2013        PMID： 24123891     DOI： 10.1002/anie.201307028

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


  9 in total

1.  Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters.

Authors:  Alexander M Haydl; John F Hartwig
Journal:  Org Lett       Date:  2019-02-14       Impact factor: 6.005

2.  Isolation, Characterization, and Reactivity of Fe8Me12(-): Kochi's S = 1/2 Species in Iron-Catalyzed Cross-Couplings with MeMgBr and Ferric Salts.

Authors:  Salvador B Muñoz Iii; Stephanie L Daifuku; William W Brennessel; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2016-06-07       Impact factor: 15.419

3.  Development and Evolution of Mechanistic Understanding in Iron-Catalyzed Cross-Coupling.

Authors:  Michael L Neidig; Stephanie H Carpenter; Daniel J Curran; Joshua C DeMuth; Valerie E Fleischauer; Theresa E Iannuzzi; Peter G N Neate; Jeffrey D Sears; Nikki J Wolford
Journal:  Acc Chem Res       Date:  2018-12-28       Impact factor: 22.384

4.  Isolation and characterization of a tetramethyliron(III) ferrate: an intermediate in the reduction pathway of ferric salts with MeMgBr.

Authors:  Malik H Al-Afyouni; Kathlyn L Fillman; William W Brennessel; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2014-10-28       Impact factor: 15.419

Review 5.  Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion.

Authors:  Alois Fürstner
Journal:  ACS Cent Sci       Date:  2016-10-27       Impact factor: 14.553

6.  Novel, male-produced aggregation pheromone of the cerambycid beetle Rosalia alpina, a priority species of European conservation concern.

Authors:  Alenka Žunič Kosi; Yunfan Zou; Michal Hoskovec; Al Vrezec; Nataša Stritih; Jocelyn G Millar
Journal:  PLoS One       Date:  2017-08-21       Impact factor: 3.240

7.  Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones.

Authors:  Matam Parameshwar; Manda Rajesh; Sridhar Balasubramanian; Maddi Sridhar Reddy
Journal:  ACS Omega       Date:  2019-10-30

8.  Lessons from Natural Product Total Synthesis: Macrocyclization and Postcyclization Strategies.

Authors:  Alois Fürstner
Journal:  Acc Chem Res       Date:  2021-01-28       Impact factor: 22.384

9.  2,6-Dicyano-4-pyrone as a Novel and Multifarious Building Block for the Synthesis of 2,6-Bis(hetaryl)-4-pyrones and 2,6-Bis(hetaryl)-4-pyridinols.

Authors:  Dmitrii L Obydennov; Alena E Simbirtseva; Sergey E Piksin; Vyacheslav Y Sosnovskikh
Journal:  ACS Omega       Date:  2020-12-15
  9 in total

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