Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway
Hoang, Kim Le Mai
Tan, Yu Jia
Date of Issue2015
School of Physical and Mathematical Sciences
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.
Angewandte chemie International edition
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