Literature DB >> 21214249

[3+2] cycloadditions of aryl cyclopropyl ketones by visible light photocatalysis.

Zhan Lu1, Meihua Shen, Tehshik P Yoon.   

Abstract

We report a new method for the formal [3+2] reaction of aryl cyclopropyl ketones with olefins to generate highly substituted cyclopentane ring systems. The key initiation step in this process is the one-electron reduction of the ketone to the corresponding radical anion, which is accomplished using a photocatalytic system comprising Ru(bpy)(3)(2+), La(OTf)(3), and TMEDA.

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Year:  2011        PMID： 21214249      PMCID： PMC3033486          DOI： 10.1021/ja107849y

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


  31 in total

1.  Photoinduced Electron Transfer Reactions of alpha-Cyclopropyl- and alpha-Epoxy Ketones. Tandem Fragmentation-Cyclization to Bi-, Tri-, and Spirocyclic Ketones.

Authors:  Thorsten Kirschberg; Jochen Mattay
Journal:  J Org Chem       Date:  1996-12-13       Impact factor: 4.354

2.  Photoredox catalysis with visible light.

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

Review 3.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
Journal:  Chem Soc Rev       Date:  2009-07-10       Impact factor: 54.564

4.  Divergent selectivity in MgI(2)-mediated ring expansions of methylenecyclopropyl amides and imides.

Authors:  Mark Lautens; Wooseok Han
Journal:  J Am Chem Soc       Date:  2002-06-05       Impact factor: 15.419

5.  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

6.  Reaction of alpha-ene-vinylcyclopropanes: type II intramolecular [5+2] cycloaddition or [3+2] cycloaddition?

Authors:  Qian Li; Guo-Jie Jiang; Lei Jiao; Zhi-Xiang Yu
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

7.  Synthesis of Linear and Angular Triquinane Skeletons by O-Stannyl Ketyl-Promoted Fragmentation-Cyclization Reactions of alpha-Keto Cyclopropanes.

Authors:  Eric J. Enholm; Zhaozhong J. Jia
Journal:  J Org Chem       Date:  1997-01-10       Impact factor: 4.354

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.  [3+2] cycloaddition reactions of cyclopropyl imines with enones.

Authors:  Lei Liu; John Montgomery
Journal:  Org Lett       Date:  2007-08-31       Impact factor: 6.005

10.  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
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  40 in total

1.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

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.  Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones.

Authors:  Adrian G Amador; Evan M Sherbrook; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

4.  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

5.  Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes.

Authors:  Barry M Trost; Patrick J Morris; Simon J Sprague
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

6.  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

7.  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

8.  Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.

Authors:  Laura Ruiz Espelt; Eric M Wiensch; Tehshik P Yoon
Journal:  J Org Chem       Date:  2013-04-10       Impact factor: 4.354

Review 9.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

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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