Literature DB >> 16433506

C-H activation as a strategic reaction: enantioselective synthesis of 4-substituted indoles.

Huw M L Davies1, James R Manning.   

Abstract

A method is described for the asymmetric synthesis of 4-substituted indoles from the Rh2(S-DOSP)4-catalyzed decomposition of vinyldiazoacetates in the presence of N-Boc-4-acetoxy-6,7-dihydroindole. The reaction proceeds via a combined C-H activation/Cope rearrangement-elimination mechanism resulting in good yields and very high asymmetric induction.

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Year:  2006        PMID: 16433506     DOI: 10.1021/ja057768+

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


  11 in total

1.  Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

Authors:  Etienne Nadeau; Dominic L Ventura; Jonathan A Brekan; Huw M L Davies
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

2.  Combined C-H functionalization/Cope rearrangement with vinyl ethers as a surrogate for the vinylogous Mukaiyama aldol reaction.

Authors:  Yajing Lian; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-07-18       Impact factor: 15.419

3.  Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

Authors:  Yajing Lian; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-30       Impact factor: 15.336

4.  Rh2(S-biTISP)2-catalyzed asymmetric functionalization of indoles and pyrroles with vinylcarbenoids.

Authors:  Yajing Lian; Huw M L Davies
Journal:  Org Lett       Date:  2012-03-27       Impact factor: 6.005

5.  Perspective on dirhodium carboxamidates as catalysts.

Authors:  Michael P Doyle
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

Review 6.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

7.  High Symmetry Dirhodium(II) Paddlewheel Complexes as Chiral Catalysts.

Authors:  Jørn Hansen; Huw M L Davies
Journal:  Coord Chem Rev       Date:  2008-03       Impact factor: 22.315

8.  The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.

Authors:  Huw M L Davies; Yajing Lian
Journal:  Acc Chem Res       Date:  2012-05-11       Impact factor: 22.384

9.  Efficient access to enantiomerically pure cyclic alpha-amino esters through a lipase-catalyzed kinetic resolution.

Authors:  Sergio Alatorre-Santamaría; María Rodriguez-Mata; Vicente Gotor-Fernández; Marcos Carlos de Mattos; Francisco J Sayago; Ana I Jiménez; Carlos Cativiela; Vicente Gotor
Journal:  Tetrahedron Asymmetry       Date:  2009-01-25

10.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

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