Literature DB >> 21666769

Visible Light Photocatalysis of Radical Anion Hetero-Diels-Alder Cycloadditions.

Anna E Hurtley1, Megan A Cismesia, Michael A Ischay, Tehshik P Yoon.   

Abstract

We have discovered a photocatalytic intramolecular hetero-Diels-Alder reaction of tethered bis(enones). This transformation involves the intermediacy of an enone radical anion and constitutes the formal coupling of an electron-deficient heterodiene with an electronically mismatched enone dienophile. The diastereoselectivity and regioselectivity of the process are high, and the dihydropyran products are amenable to a variety of synthetically useful transformations.

Entities:  

Year:  2011        PMID： 21666769      PMCID： PMC3110713          DOI： 10.1016/j.tet.2011.02.066

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  33 in total

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2.  Total synthesis, configuration, and biological evaluation of anguinomycin C.

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3.  Photoredox catalysis with visible light.

Authors:  Kirsten Zeitler
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Anion radical chain cycloaddition of tethered enones: intramolecular cyclobutanation and Diels-Alder cycloaddition.

Authors:  Yeonsuk Roh; Hye-Young Jang; Vincent Lynch; Nathan L Bauld; Michael J Krische
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

5.  A catalytic enantioselective hetero Diels-Alder approach to the C20-C32 segment of the phorboxazoles.

Authors:  Brian S Lucas; Laura M Luther; Steven D Burke
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

6.  Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

Authors:  Hui-Wen Shih; Mark N Vander Wal; Rebecca L Grange; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

7.  Total synthesis of the microtubule-stabilizing agent (-)-laulimalide.

Authors:  I Paterson; C De Savi; M Tudge
Journal:  Org Lett       Date:  2001-10-04       Impact factor: 6.005

8.  Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates.

Authors:  Laura Furst; Bryan S Matsuura; Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

9.  Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis.

Authors:  Juana Du; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

10.  Enantioselective total synthesis of macrolide antitumor agent (-)-lasonolide A.

Authors:  Arun K Ghosh; Gangli Gong
Journal:  Org Lett       Date:  2007-03-17       Impact factor: 6.005
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  23 in total

1.  Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light.

Authors:  David B Freeman; Laura Furst; Allison G Condie; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-12-08       Impact factor: 6.005

Review 2.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

3.  Visible-light photoredox catalysis in flow.

Authors:  Joseph W Tucker; Yuan Zhang; Timothy F Jamison; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-16       Impact factor: 15.336

4.  Recent developments in transition-metal photoredox-catalysed reactions of carbonyl derivatives.

Authors:  Katarzyna N Lee; Ming-Yu Ngai
Journal:  Chem Commun (Camb)       Date:  2017-12-07       Impact factor: 6.222

5.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

6.  Intermolecular [3+2] cycloaddition of cyclopropylamines with olefins by visible-light photocatalysis.

Authors:  Soumitra Maity; Mingzhao Zhu; Ryan Spencer Shinabery; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-23       Impact factor: 15.336

7.  [2+2] cycloaddition of 1,3-dienes by visible light photocatalysis.

Authors:  Anna E Hurtley; Zhan Lu; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-01       Impact factor: 15.336

8.  Catalytic Radical Domino Reactions in Organic Synthesis.

Authors:  Leanne J Sebren; James J Devery; Corey R J Stephenson
Journal:  ACS Catal       Date:  2014-02-07       Impact factor: 13.084

9.  Transition metal photoredox catalysis of radical thiol-ene reactions.

Authors:  Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal:  J Org Chem       Date:  2012-11-12       Impact factor: 4.354

10.  Visible light photocatalysis of [2+2] styrene cycloadditions by energy transfer.

Authors:  Zhan Lu; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-10       Impact factor: 15.336
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