Literature DB >> 19580273

Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Alexander M Taylor1, Ryan A Altman, Stephen L Buchwald.   

Abstract

The enantioselective alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are formed in high enantiomeric excess, and the conditions tolerate a range of substitution on both the oxindole and the aryl/vinyl coupling partners.

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Year:  2009        PMID： 19580273      PMCID： PMC2782534          DOI： 10.1021/ja903880q

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


  26 in total

1.  Catalytic asymmetric vinylation of ketone enolates.

Authors:  A Chieffi; K Kamikawa; J Ahman; J M Fox; S L Buchwald
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

2.  Enantioselective Construction of Quaternary Stereocenters.

Authors:  Jens Christoffers; Alexander Mann
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

3.  Bulky chiral carbene ligands and their application in the palladium-catalyzed asymmetric intramolecular alpha-arylation of amides.

Authors:  E Peter Kündig; Thomas M Seidel; Yi-Xia Jia; Gérald Bernardinelli
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  An improved catalyst for the asymmetric arylation of ketone enolates.

Authors:  Takayuki Hamada; André Chieffi; Jens Ahman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-02-20       Impact factor: 15.419

5.  Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones.

Authors:  Dirk J Spielvogel; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-04-10       Impact factor: 15.419

6.  Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles.

Authors:  Ryan A Altman; Alan M Hyde; Xiaohua Huang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-06-28       Impact factor: 15.419

7.  AcOLeDMAP and BnOLeDMAP: conformationally restricted nucleophilic catalysts for enantioselective rearrangement of indolyl acetates and carbonates.

Authors:  Trisha A Duffey; Scott A Shaw; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

8.  Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

Authors:  Xuebin Liao; Zhiqiang Weng; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-12-13       Impact factor: 15.419

9.  Palladium-catalyzed alpha-vinylation of carbonyl compounds.

Authors:  Jinkun Huang; Emilio Bunel; Margaret M Faul
Journal:  Org Lett       Date:  2007-09-22       Impact factor: 6.005

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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  37 in total

1.  Alpha-arylation of 3-aryloxindoles.

Authors:  Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

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.  Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes: effect of halide on selectivity, oxidation state, and room-temperature reactions.

Authors:  Shaozhong Ge; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

5.  Palladium(0)-catalyzed arylative dearomatization of phenols.

Authors:  Sophie Rousseaux; Jorge García-Fortanet; Miguel Angel Del Aguila Sanchez; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2011-05-25       Impact factor: 15.419

6.  Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids.

Authors:  Marc Liniger; Yiyang Liu; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-09-25       Impact factor: 15.419

7.  A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Synthesis of catalyst libraries and evaluation of catalyst activity.

Authors:  Scott E Denmark; Nathan D Gould; Larry M Wolf
Journal:  J Org Chem       Date:  2011-05-06       Impact factor: 4.354

8.  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

9.  Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins.

Authors:  Lun Li; Kimberly A Wasik; Brian J Frost; Laina M Geary
Journal:  Tetrahedron Lett       Date:  2019-11-06       Impact factor: 2.415

10.  Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236
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