Literature DB >> 25695366

Amide and amine nucleophiles in polar radical crossover cycloadditions: synthesis of γ-lactams and pyrrolidines.

Nathan J Gesmundo1, Jean-Marc M Grandjean, David A Nicewicz.   

Abstract

In this work we present a direct catalytic synthesis of γ-lactams and pyrrolidines from alkenes and activated unsaturated amides or protected unsaturated amines, respectively. Using a mesityl acridinium single electron photooxidant and a thiophenol cocatalyst under irradiation, we are able to directly forge these important classes of heterocycles with complete regiocontrol.

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Year:  2015        PMID: 25695366     DOI: 10.1021/acs.orglett.5b00316

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  11 in total

1.  Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.

Authors:  Chanchamnan Um; Sherry R Chemler
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

2.  Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.

Authors:  Shishi Lin; Shane D Lies; Christopher S Gravatt; Tehshik P Yoon
Journal:  Org Lett       Date:  2016-12-29       Impact factor: 6.005

3.  Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation.

Authors:  Timothy M Monos; Rory C McAtee; Corey R J Stephenson
Journal:  Science       Date:  2018-09-28       Impact factor: 63.714

4.  Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer.

Authors:  David C Miller; Gilbert J Choi; Hudson S Orbe; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2015-10-16       Impact factor: 15.419

5.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

Review 6.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622

7.  Metal-free C-H alkylation of heteroarenes with alkyltrifluoroborates: a general protocol for 1°, 2° and 3° alkylation.

Authors:  Jennifer K Matsui; David N Primer; Gary A Molander
Journal:  Chem Sci       Date:  2017-03-06       Impact factor: 9.825

8.  Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins.

Authors:  Pablo Bonilla; Yannick P Rey; Catherine M Holden; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-31       Impact factor: 15.336

Review 9.  Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis.

Authors:  Rik H Verschueren; Wim M De Borggraeve
Journal:  Molecules       Date:  2019-06-05       Impact factor: 4.411

Review 10.  A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones.

Authors:  Joonseong Hur; Jaebong Jang; Jaehoon Sim
Journal:  Int J Mol Sci       Date:  2021-03-09       Impact factor: 5.923

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