Literature DB >> 17177383

Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and beta-keto esters using DBFOX ligand.

Takehisa Ishimaru1, Norio Shibata, Jun Nagai, Shuichi Nakamura, Takeshi Toru, Shuji Kanemasa.   

Abstract

The first catalytic enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2-oxindoles using the DBFOX-Zn(II) complex, leading to pharmaceutically important chiral 3-hydroxy-2-oxindoles was described. The structure of oxidant was found to play an important role to increase the enantioselectivity. The methodology has successfully applied to the highly enantioselective hydroxylation of beta-keto esters using the DBFOX-Ni(II) complex.

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Year:  2006        PMID: 17177383     DOI: 10.1021/ja0668825

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


  13 in total

1.  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

2.  Iron-catalyzed aminohydroxylation of olefins.

Authors:  Kevin S Williamson; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

3.  Highly enantioselective catalytic benzoyloxylation of 3-aryloxindoles using chiral VAPOL calcium phosphate.

Authors:  Zuhui Zhang; Wenhua Zheng; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-22       Impact factor: 15.336

4.  Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.

Authors:  Hai-Jun Zhang; Alexander W Schuppe; Shi-Tao Pan; Jin-Xiang Chen; Bo-Ran Wang; Timothy R Newhouse; Liang Yin
Journal:  J Am Chem Soc       Date:  2018-04-09       Impact factor: 15.419

5.  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

6.  Catalytic enantioselective O-nitrosocarbonyl aldol reaction of β-dicarbonyl compounds.

Authors:  Mahiuddin Baidya; Kimberly A Griffin; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2012-11-02       Impact factor: 15.419

7.  Iron catalyzed asymmetric oxyamination of olefins.

Authors:  Kevin S Williamson; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

8.  Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone.

Authors:  Jin-Sheng Yu; Feng Zhou; Yun-Lin Liu; Jian Zhou
Journal:  Beilstein J Org Chem       Date:  2012-08-23       Impact factor: 2.883

9.  Advances in the chemistry of oxaziridines.

Authors:  Kevin S Williamson; David J Michaelis; Tehshik P Yoon
Journal:  Chem Rev       Date:  2014-04-22       Impact factor: 60.622

Review 10.  Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Authors:  Johannes Schörgenhumer; Maximilian Tiffner; Mario Waser
Journal:  Beilstein J Org Chem       Date:  2017-08-22       Impact factor: 2.883

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