Literature DB >> 20349945

Highly chemo- and enantioselective synthesis of 3-allyl-3-aryl oxindoles via the direct palladium-catalyzed alpha-arylation of amides.

Xinjun Luan1, Linglin Wu, Emma Drinkel, Ronaldo Mariz, Michele Gatti, Reto Dorta.   

Abstract

A new NHC x Pd-catalyzed asymmetric alpha-arylation of amides is reported that gives direct access to synthetically valuable, allylated oxindoles with quaternary carbon centers. The reaction is made possible by the introduction of a new chiral NHC ligand. The palladium complexes derived therefrom combine excellent reactivity with high chemo- and enantioselectivity for the title transformation.

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Year:  2010        PMID: 20349945     DOI: 10.1021/ol1003093

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


  6 in total

1.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

2.  Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

Authors:  Trung Cao; Joshua Deitch; Elizabeth C Linton; Marisa C Kozlowski
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

3.  A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Authors:  Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

4.  Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Authors:  Hwan Jung Lim; T V RajanBabu
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

5.  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

6.  Synthesis and biological evaluation of achiral indole-substituted titanocene dichloride derivatives.

Authors:  Anthony Deally; Frauke Hackenberg; Grainne Lally; Matthias Tacke
Journal:  Int J Med Chem       Date:  2012-06-12
  6 in total

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