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Reversing the Stereoselectivity of a Palladium‐Catalyzed O‐Glycosylation through an Inner‐Sphere or Outer‐Sphere Pathway
Author(s) -
Xiang Shaohua,
Hoang Kim Le Mai,
He Jingxi,
Tan Yu Jia,
Liu XueWei
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408739
Subject(s) - nucleophile , chemistry , palladium , stereoselectivity , anomer , glucal , glycosylation , glycosidic bond , catalysis , phenol , coordination sphere , stereochemistry , organic chemistry , molecule , enzyme , biochemistry
An efficient and concise method for the construction of various O‐glycosidic bonds by a palladium‐catalyzed reaction with a 3‐O‐picoloyl glucal has been developed. The stereochemistry of the anomeric center derives from either an inner‐sphere or outer‐sphere pathway. Harder nucleophiles, such as aliphatic alcohols and sodium phenoxides give β‐products, and α products result from using softer nucleophiles, such as phenol.