Literature DB >> 25983348

Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters.

Chung Whan Lee1, Seo-Jung Han1, Scott C Virgil1, Brian M Stoltz1.   

Abstract

An improved method for the asymetric alkylation of 3-bromooxindoles with α-arylated malonate esters is described. The asymmetric alkylation demonstrated was achieved up to 70% ee utilizing a copper(II) bis(phosphine) complex.

Entities:  

Keywords:  3,3-Disubstituted oxindole; Asymmetric catalysis; Chiral bis(phosphine) ligands; Copper catalysis

Year:  2015        PMID： 25983348      PMCID： PMC4429905          DOI： 10.1016/j.tet.2014.10.065

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  45 in total

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5.  Palladium-catalyzed asymmetric construction of vicinal all-carbon quaternary stereocenters and its application to the synthesis of cyclotryptamine alkaloids.

Authors:  Barry M Trost; Maksim Osipov
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-03       Impact factor: 15.336

6.  Palladium-catalyzed asymmetric benzylation of 3-aryl oxindoles.

Authors:  Barry M Trost; Lara C Czabaniuk
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

7.  Total synthesis of (+)-perophoramidine and determination of the absolute configuration.

Authors:  Haoxing Wu; Fei Xue; Xue Xiao; Yong Qin
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

8.  Ionic nucleophilic catalysis of chiral ammonium betaines for highly stereoselective aldol reaction from oxindole-derived vinylic carbonates.

Authors:  Daisuke Uraguchi; Kyohei Koshimoto; Takashi Ooi
Journal:  J Am Chem Soc       Date:  2012-04-12       Impact factor: 15.419

9.  Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at the C3 position.

Authors:  Feng Zhou; Xing-Ping Zeng; Chao Wang; Xiao-Li Zhao; Jian Zhou
Journal:  Chem Commun (Camb)       Date:  2013-03-11       Impact factor: 6.222

Review 10.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
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  3 in total

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Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

2.  Evolution of a unified, stereodivergent approach to the synthesis of communesin F and perophoramidine.

Authors:  Seo-Jung Han; Florian Vogt; Jeremy A May; Shyam Krishnan; Michele Gatti; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2014-11-26       Impact factor: 4.354

3.  Palladium-catalysed formation of vicinal all-carbon quaternary centres via propargylation.

Authors:  Xin Huang; Shangze Wu; Wangteng Wu; Pengbin Li; Chunling Fu; Shengming Ma
Journal:  Nat Commun       Date:  2016-08-25       Impact factor: 14.919
  3 in total

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