Functionalization of the Anomeric C–H Bond of Carbohydrates: Old Strategies and New Opportunities

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

Key words

C–H bond functionalization - carbohydrates - molecular diversity - carbenes - 1,5-insertion

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