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Synlett 2013; 24(19): 2477-2491
DOI: 10.1055/s-0033-1339317
DOI: 10.1055/s-0033-1339317
account
Functionalization of the Anomeric C–H Bond of Carbohydrates: Old Strategies and New Opportunities
Further Information
Publication History
Received: 25 March 2013
Accepted after revision: 05 June 2013
Publication Date:
09 October 2013 (online)
Abstract
After a quick review of the existing methods that enable the quaternarization of the anomeric position of carbohydrates via a C–H bond functionalization process, we summarize recent contributions from our group related to the preparation of α- and β-ketopyranosides by the 1,5-insertion of metal carbenes.
1 Introduction
2 Early Developments: Anchoring of Reactive Species at the Anomeric Position
2.1 Radical-Promoted Quaternarization of the Anomeric Position
2.2 Photochemically Induced Quaternarization of the Anomeric Position
2.3 Alkylidene-Promoted Quaternarization of the Anomeric Position
2.4 Nitrene-Promoted Quaternarization of the Anomeric Position
2.5 Any Possible Extension to the Preparation of α- and β-Ketopyranosides?
3 Carbene-Mediated Functionalization of the Anomeric C–H Bond of Carbohydrates
3.1 Functionalization of Carbohydrate Scaffolds by the Insertion of Metal Carbenes: A Challenging Task
3.2 Preparation of Carbene Precursors
3.3 Transition Metal Catalyzed Decomposition of Diazo Sugars
3.4 Dramatic Effects of Molecular Sieves
3.5 Ring Opening of γ-Lactones
4 Development of a Stereoselective Glycosylation/Diazo Transfer/Quaternarization Sequence
4.1 Preliminary Studies with a Permethylated Acceptor
4.2 Stereoselective Access to Quaternary Disaccharides: Scope and Limitations
5 Concluding Remarks
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For leading reviews, see:
For recent reviews, see:
For special issues dedicated to C–H bond functionalization, see:
For reviews on the synthesis of biologically active compounds and natural products, see:
For reviews on C–H bond functionalization as a source of molecular diversity, see:
For reviews on the biological implications of carbohydrates, see:
For reviews on new synthetic methods and chemical tools, see:
For recent reports on C–H bond functionalization in carbohydrate chemistry, see:
For an alternative strategy involving closure of the sugar ring as a key step, see:
For leading references, see:
For efficient access to α-ketopyranosides based on a Ferrier-type rearrangement, see:
For leading references on metal-carbene-mediated C–H functionalization processes, see:
For reviews on carbene-mediated C–H functionalization processes, see:
For fine tuning the reactivity of rhodium(II) carbenes through the ligands, see: