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Literature DB >> 18942849

Nucleophilic addition of potassium alkynyltrifluoroborates to D-glucal mediated by BF3 x OEt2: highly stereoselective synthesis of alpha-C-glycosides.

Adriano S Vieira¹, Pedro F Fiorante, Thomas L S Hough, Fernando P Ferreira, Diogo S Lüdtke, Hélio A Stefani.

Abstract

A convenient, mild and highly stereoselective method for C-glycosidation (alkynylation) of D-glucal with various potassium alkynyltrifluoroborates, mediated by BF3x OEt2 and involving oxonium intermediates, preferentially provides the alpha-acetylene glycoside products with good yields.

Entities: Chemical

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Year: 2008 PMID： 18942849 DOI： 10.1021/ol8022177

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

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Cited

14 in total

1. Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

Authors: Harathi D Srinivas; Prantik Maity; Glenn P A Yap; Mary P Watson
Journal: J Org Chem Date: 2015-04-07 Impact factor: 4.354

2. Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

Authors: Prantik Maity; Harathi D Srinivas; Mary P Watson
Journal: J Am Chem Soc Date: 2011-10-11 Impact factor: 15.419

3. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal.

Authors: Anwar Shamim; Frederico B Souza; Gustavo H G Trossini; Fernando M Gatti; Hélio A Stefani
Journal: Mol Divers Date: 2015-01-14 Impact factor: 2.943

4. Stereoselective C-glycosidations with achiral and enantioenriched allenylsilanes.

Authors: Ryan A Brawn; James S Panek
Journal: Org Lett Date: 2010-10-15 Impact factor: 6.005

5. Aromatic cations from oxidative carbon-hydrogen bond cleavage in bimolecular carbon-carbon bond forming reactions.

Authors: Dane J Clausen; Paul E Floreancig
Journal: J Org Chem Date: 2012-07-16 Impact factor: 4.354

6. Expanded substrate scope and improved reactivity of ether-forming cross-coupling reactions of organotrifluoroborates and acetals.

Authors: Cam-Van T Vo; T Andrew Mitchell; Jeffrey W Bode
Journal: J Am Chem Soc Date: 2011-08-17 Impact factor: 15.419

Nucleophilic addition of potassium alkynyltrifluoroborates to D-glucal mediated by BF3 x OEt2: highly stereoselective synthesis of alpha-C-glycosides.

1. Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

2. Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

3. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal.

4. Stereoselective C-glycosidations with achiral and enantioenriched allenylsilanes.

5. Aromatic cations from oxidative carbon-hydrogen bond cleavage in bimolecular carbon-carbon bond forming reactions.

6. Expanded substrate scope and improved reactivity of ether-forming cross-coupling reactions of organotrifluoroborates and acetals.

7. TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes.

8. Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.

9. A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes.

10. Metal-free synthesis of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts.