Premium
Stereospecific C‐Glycosylation by Mizoroki–Heck Reaction: A Powerful and Easy‐to‐Set‐Up Synthetic Tool to Access α ‐ and β ‐Aryl‐ C ‐Glycosides
Author(s) -
Mabit Thibaud,
Siard Aymeric,
Legros Frédéric,
Guillarme Stéphane,
Martel Arnaud,
Lebreton Jacques,
Carreaux François,
Dujardin Gilles,
Collet Sylvain
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803674
Subject(s) - stereospecificity , glycosylation , aryl , chemistry , glycoside , heck reaction , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , alkyl
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.