Literature DB >> 22185609

N-Heterocyclic carbene catalyzed C-glycosylation: a concise approach from Stetter reaction.

Seenuvasan Vedachalam1, Shi Min Tan, Hui Ping Teo, Shuting Cai, Xue-Wei Liu.   

Abstract

Described herein is the first example of an organocatalytic approach for acylanion addition to the anomeric carbon of 2-nitroglucal using an N-heterocyclic carbene catalyst. Control over the reaction conditions gives β-selective and nitro-eliminated C-glycosides, providing opportunities to produce new classes of C-glycoside.
© 2011 American Chemical Society

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Year:  2011        PMID: 22185609     DOI: 10.1021/ol202959y

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

Review 2.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

3.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

4.  Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors.

Authors:  Mukta Shaw; Yogesh Kumar; Rima Thakur; Amit Kumar
Journal:  Beilstein J Org Chem       Date:  2017-11-09       Impact factor: 2.883

5.  Investigation of the Selectivity of the Palladium-Catalyzed Aroylation and Arylation of Stannyl Glycals with Aroyl Chlorides.

Authors:  Tsuyoshi Shinozuka
Journal:  ACS Omega       Date:  2021-03-19

6.  Synthesis of Hydrophobic Carbohydrate Polymers and Their Formation of Thermotropic Liquid Crystalline Phases.

Authors:  Cynthia Ghobril; Benoît Heinrich; Eric L Dane; Mark W Grinstaff
Journal:  ACS Macro Lett       Date:  2014-03-27       Impact factor: 6.903

  6 in total

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