Literature DB >> 19455525

Phosphonium salts as chiral phase-transfer catalysts: asymmetric Michael and Mannich reactions of 3-aryloxindoles.

Rongjun He1, Changhua Ding, Keiji Maruoka.   

Abstract

It's a PTC: A highly efficient reaction of 3-aryloxindoles in an asymmetric Michael addition was achieved by using a quaternary tetraalkylphosphonium salt as a chiral phase-transfer catalyst (PTC). The products were obtained in quantitative yields high ee values. The reaction of 3-aryloxindoles in an asymmetric Mannich reaction using the same catalyst also proved to be feasible.

Entities:  

Year:  2009        PMID: 19455525     DOI: 10.1002/anie.200901277

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  18 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.  Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors:  Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

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.  Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

Authors:  Wenhua Zheng; Zuhui Zhang; Matthew J Kaplan; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

5.  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

6.  Construction of bispirooxindoles containing three quaternary stereocentres in a cascade using a single multifunctional organocatalyst.

Authors:  Bin Tan; Nuno R Candeias; Carlos F Barbas
Journal:  Nat Chem       Date:  2011-05-08       Impact factor: 24.427

7.  Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

8.  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

9.  Palladium-catalyzed asymmetric allylic alkylation of 3-aryloxindoles with allylidene dipivalate: a useful enol pivalate product.

Authors:  Barry M Trost; James T Masters; Aaron C Burns
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-17       Impact factor: 15.336

10.  A Copper-Catalyzed Arylation of Tryptamines for the Direct Synthesis of Aryl Pyrroloindolines.

Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal:  Chem Sci       Date:  2012-11       Impact factor: 9.825

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