Literature DB >> 20121078

Rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles.

Yajing Lian1, Huw M L Davies.   

Abstract

An unusual rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles is described. These studies show that (Z)-vinylcarbenoids have a greater tendency than (E)-vinylcarbenoids to react at the vinylogous position of the carbenoid rather than at the carbenoid center.

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Year:  2010        PMID： 20121078      PMCID： PMC2921947          DOI： 10.1021/ol9028385

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


  20 in total

1.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Cyclizations of N-acyliminium ions.

Authors:  Bruce E Maryanoff; Han-Cheng Zhang; Judith H Cohen; Ignatius J Turchi; Cynthia A Maryanoff
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

3.  Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

4.  Tandem catalytic asymmetric Friedel-Crafts/Henry reaction: control of three contiguous acyclic stereocenters.

Authors:  Takayoshi Arai; Naota Yokoyama
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Investigation into factors influencing stereoselectivity in the reactions of heterocycles with donor-acceptor-substituted rhodium carbenoids.

Authors:  Simon J Hedley; Dominic L Ventura; Paulina M Dominiak; Cara L Nygren; Huw M L Davies
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

6.  Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis.

Authors:  Joel F Austin; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-02-20       Impact factor: 15.419

Review 7.  Intermolecular reactions of electron-rich heterocycles with copper and rhodium carbenoids.

Authors:  Huw M L Davies; Simon J Hedley
Journal:  Chem Soc Rev       Date:  2007-02-15       Impact factor: 54.564

8.  Selective tryptophan modification with rhodium carbenoids in aqueous solution.

Authors:  John M Antos; Matthew B Francis
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419

9.  Highly diastereoselective sulfonium ylide rearrangements to quaternary substituted indolines.

Authors:  Vyacheslav Boyarskikh; Abijah Nyong; Jon D Rainier
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Enantioselective Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.

Authors:  David A Evans; Keith R Fandrick; Hyun-Ji Song; Karl A Scheidt; Risheng Xu
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419
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  10 in total

1.  Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.

Authors:  Xiaochen Wang; Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

2.  Rh2(R-TPCP)4-catalyzed enantioselective [3+2]-cycloaddition between nitrones and vinyldiazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2013-09-20       Impact factor: 15.419

3.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

4.  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

5.  Alkynoate synthesis through the vinylogous reactivity of rhodium(II) carbenoids.

Authors:  Damien Valette; Yajing Lian; John P Haydek; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-16       Impact factor: 15.336

6.  Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds.

Authors:  Yongming Deng; Lynée A Massey; Yeray A Rodriguez Núñez; Hadi Arman; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-24       Impact factor: 15.336

7.  An atom-economic synthesis of nitrogen heterocycles from alkynes.

Authors:  Barry M Trost; Jean-Philip Lumb; Joseph M Azzarelli
Journal:  J Am Chem Soc       Date:  2011-02-02       Impact factor: 15.419

8.  Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

Authors:  Andrew DeAngelis; Valerie W Shurtleff; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2011-01-25       Impact factor: 15.419

9.  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

10.  Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles.

Authors:  Kai Liu; Guangyang Xu; Jiangtao Sun
Journal:  Chem Sci       Date:  2017-11-06       Impact factor: 9.825
  10 in total

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