Stereospecific C-Glycosylation by Mizoroki-Heck Reaction A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides

Thibaud Mabit; Aymeric Siard; Frédéric Legros; Stéphane Guillarme; Arnaud Martel; Jacques Lebreton; François Carreaux; Gilles Dujardin; Sylvain Collet

Stereospecific C-Glycosylation by Mizoroki-Heck Reaction A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides

Thibaud Mabit ^{1, 2} Aymeric Siard ¹ Frédéric Legros ² Stéphane Guillarme ³ Arnaud Martel ³ Jacques Lebreton ¹ François Carreaux ⁴ Gilles Dujardin ³ Sylvain Collet ¹

1 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

2 IMMM - Institut des Molécules et Matériaux du Mans

3 UCO2M - Unité de chimie organique moléculaire et macromoléculaire

4 ISCR - Institut des Sciences Chimiques de Rennes

Abstract : A stereospecific Mizoroki-Heck cross-coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either α- or β-aryl-C-glycosides depending solely on the configuration at C3 was achieved. The reaction was easy to set up because no specific precautions were required concerning moisture or oxygen, and it proceeded by a chirality transfer from C3 to C1. After optimization of cross-coupling conditions, various prepared glycals (7 examples) and arenes (10 examples) were tested, leading stereospecifically to the corresponding aryl-C-glycosides with a carbonyl group at C3, thus opening up new horizons for the total synthesis of glycosylated natural products.

Keywords : C-glycosides Mizoroki-Heck reaction cross-coupling α-glycosylation β-glycosylation

Document type :

Journal articles

Domain :

Chemical Sciences

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Stereospecific C-Glycosylation by Mizoroki-Heck Reaction A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides

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Stereospecific C-Glycosylation by Mizoroki-Heck Reaction A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides

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