Literature DB >> 19290662

Chiral Brønsted acid-catalyzed enantioselective alpha-hydroxylation of beta-dicarbonyl compounds.

Min Lu1, Di Zhu, Yunpeng Lu, Xiaofei Zeng, Bin Tan, Zhenjiang Xu, Guofu Zhong.   

Abstract

A novel, facile, and highly enantioselective Brønsted acid-catalyzed alpha-hydroxylation of beta-dicarbonyl compounds with up to 99:1 er using nitroso compounds as the oxygen source has been developed. The results disclosed herein considerably extend the substrate scope for the alpha-aminoxylation, allowing expeditious, straightforward, and efficient access to valuable alpha-hydroxy-beta-dicarbonyl compounds with the highest levels of enantiocontrol.

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Year:  2009        PMID: 19290662     DOI: 10.1021/ja8088907

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


  5 in total

1.  Chiral phosphoric acid catalyzed peroxidation of imines.

Authors:  Wenhua Zheng; Lukasz Wojtas; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-03       Impact factor: 15.336

2.  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

Review 3.  Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

Authors:  Tirayut Vilaivan; Worawan Bhanthumnavin
Journal:  Molecules       Date:  2010-02-11       Impact factor: 4.411

4.  Organocatalytic asymmetric nitroso aldol reaction of α-substituted malonamates.

Authors:  Ekta Gupta; Narendra Kumar Vaishanv; Sandeep Kumar; Raja Krishnan Purshottam; Ruchir Kant; Kishor Mohanan
Journal:  Beilstein J Org Chem       Date:  2022-02-21       Impact factor: 2.883

Review 5.  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

  5 in total

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