Literature DB >> 19170565

Sn-free Ni-catalyzed reductive coupling of glycosyl bromides with activated alkenes.

Hegui Gong1, R Stephen Andrews, Joseph L Zuccarello, Stephen J Lee, Michel R Gagné.   

Abstract

A mild, stereoselective method for the Ni-catalyzed synthesis of alpha-C-alkylglycosides is reported. This approach entails the reductive coupling of glycosyl bromides with activated alkenes at room temperature, with low alkene loading as an important feature. Diastereoselective coupling with 2-substituted acrylate derivatives was made possible through the use of 2,4-dimethyl-3-pentanol as a proton source.

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Year:  2009        PMID: 19170565     DOI: 10.1021/ol8028737

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


  3 in total

1.  Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors:  Matthew J McKay; Hien M Nguyen
Journal:  ACS Catal       Date:  2012-06-14       Impact factor: 13.084

Review 2.  Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Authors:  Anastasia L Gant Kanegusuku; Jennifer L Roizen
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-21       Impact factor: 16.823

3.  Visible light-driven Giese reaction with alkyl tosylates catalysed by nucleophilic cobalt.

Authors:  Kimihiro Komeyama; Takuya Michiyuki; Yoshikazu Teshima; Itaru Osaka
Journal:  RSC Adv       Date:  2021-01-18       Impact factor: 3.361

  3 in total

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