Literature DB >> 16448093

Highly enantioselective synthesis of tetrahydro-beta-carbolines and tetrahydro-gamma-carbolines via Pd-catalyzed intramolecular allylic alkylation.

Marco Bandini1, Alfonso Melloni, Fabio Piccinelli, Riccardo Sinisi, Simona Tommasi, Achille Umani-Ronchi.   

Abstract

A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses (ee up to 97%).

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Year:  2006        PMID： 16448093     DOI： 10.1021/ja054109o

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


  12 in total

1.  Thiourea-catalyzed enantioselective iso-Pictet-Spengler reactions.

Authors:  Yunmi Lee; Rebekka S Klausen; Eric N Jacobsen
Journal:  Org Lett       Date:  2011-09-15       Impact factor: 6.005

2.  Palladium-catalyzed C3-benzylation of indoles.

Authors:  Ye Zhu; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-12-09       Impact factor: 15.419

3.  Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles.

Authors:  Thomas D Montgomery; Ye Zhu; Natsuko Kagawa; Viresh H Rawal
Journal:  Org Lett       Date:  2013-02-21       Impact factor: 6.005

4.  Iridium-catalyzed regio- and enantioselective N-allylation of indoles.

Authors:  Levi M Stanley; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.

Authors:  Natsuko Kagawa; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2008-05-21       Impact factor: 6.005

6.  Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles.

Authors:  Xiao Zhang; Wen-Bo Liu; Hang-Fei Tu; Shu-Li You
Journal:  Chem Sci       Date:  2015-06-08       Impact factor: 9.825

7.  Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding.

Authors:  Qing-Feng Wu; Chao Zheng; Chun-Xiang Zhuo; Shu-Li You
Journal:  Chem Sci       Date:  2016-03-29       Impact factor: 9.825

8.  Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation.

Authors:  Matteo Faltracco; Silvia Cotogno; Christophe M L Vande Velde; Eelco Ruijter
Journal:  J Org Chem       Date:  2019-09-10       Impact factor: 4.354

9.  Palladium-catalyzed dual C-H or N-H functionalization of unfunctionalized indole derivatives with alkenes and arenes.

Authors:  Gianluigi Broggini; Egle M Beccalli; Andrea Fasana; Silvia Gazzola
Journal:  Beilstein J Org Chem       Date:  2012-10-11       Impact factor: 2.883

10.  Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate.

Authors:  Thomas D Montgomery; Antoinette E Nibbs; Ye Zhu; Viresh H Rawal
Journal:  Org Lett       Date:  2014-06-25       Impact factor: 6.005
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