Stereospecific C-Glycosylation by Mizoroki-Heck Reaction A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides - Archive ouverte HAL Access content directly
Journal Articles Chemistry - A European Journal Year : 2018

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

(1, 2) , (1) , (2) , (2) , (2) , (1) , (3) , (2) , (1)
1
2
3

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.
Fichier principal
Vignette du fichier
Mabit et al_Stereospecific C-glycosylation via Mizoroki-Heck reaction, a powerful and.pdf (2.21 Mo) Télécharger le fichier
Origin : Files produced by the author(s)
Loading...

Dates and versions

hal-01863769 , version 1 (12-09-2018)

Identifiers

Cite

Thibaud Mabit, Aymeric Siard, Frédéric Legros, Stéphane Guillarme, Arnaud Martel, et al.. Stereospecific C-Glycosylation by Mizoroki-Heck Reaction A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides. Chemistry - A European Journal, 2018, 24 (53), pp.14069-14074. ⟨10.1002/chem.201803674⟩. ⟨hal-01863769⟩
79 View
177 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More