Literature DB >> 23391477

Pd-catalyzed asymmetric allylic alkylations of 3-substituted indoles using chiral P/olefin ligands.

Yilin Liu1, Haifeng Du.   

Abstract

A palladium-catalyzed asymmetric allylic alkylation of 3-substituted indoles using P/olefin ligands was successfully achieved to afford a variety of indolenines containing a quaternary carbon stereocenter in high yields with up to 87% ee. Significantly, this reaction provides a concise access to a stereoisomer of the natural product Angelicastigmin.

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Year:  2013        PMID: 23391477     DOI: 10.1021/ol3032736

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


  10 in total

1.  Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors:  Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-06       Impact factor: 15.336

2.  Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

Authors:  Santanu Panda; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2017-04-21       Impact factor: 15.419

3.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

4.  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

5.  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

6.  BF3-OEt2 Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies.

Authors:  Iqbal N Shaikh; Abdul Rahim; Shaikh Faazil; Syed Farooq Adil; Mohamed E Assal; Mohammad Rafe Hatshan
Journal:  Molecules       Date:  2021-04-11       Impact factor: 4.411

7.  Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity.

Authors:  Zhen Zhang; Sneha Ray; Leah Imlay; Lauren T Callaghan; Hanspeter Niederstrasser; Prema Latha Mallipeddi; Bruce A Posner; Dawn M Wetzel; Margaret A Phillips; Myles W Smith
Journal:  Chem Sci       Date:  2021-06-30       Impact factor: 9.825

8.  Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen.

Authors:  Jose R Cabrero-Antonino; Rosa Adam; Kathrin Junge; Matthias Beller
Journal:  Chem Sci       Date:  2017-07-26       Impact factor: 9.825

9.  Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.

Authors:  Song Yang; Quan-Zhe Li; Chen Xu; Qin Xu; Min Shi
Journal:  Chem Sci       Date:  2018-05-11       Impact factor: 9.825

10.  Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.

Authors:  James A Rossi-Ashton; Aimee K Clarke; James R Donald; Chao Zheng; Richard J K Taylor; William P Unsworth; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

  10 in total

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