We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Stereospecific C‐Glycosylation by Mizoroki–Heck Reaction: A Powerful and Easy‐to‐Set‐Up Synthetic Tool to Access α‐ and β‐Aryl‐C‐Glycosides.
- Authors
Mabit, Thibaud; Siard, Aymeric; Legros, Frédéric; Guillarme, Stéphane; Martel, Arnaud; Lebreton, Jacques; Carreaux, François; Dujardin, Gilles; Collet, Sylvain
- Abstract
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.
- Subjects
GLYCOSYLATION; GLYCOSIDES; ARYL halides; COUPLING reactions (Chemistry); GLYCALS
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 53, p14069
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201803674