Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway

• Main Authors: Xiang, Shaohua, Hoang, Kim Le Mai, He, Jingxi, Tan, Yu Jia, Liu, Xue-Wei
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2015
• Subjects: DRNTU::Science::Chemistry::Physical chemistry::Stereochemistry
• Online Access: https://hdl.handle.net/10356/106703; http://hdl.handle.net/10220/25100; http://dx.doi.org/10.1002/anie.201408739
• Institution: Nanyang Technological University

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 ali...