Premium
Selective C−O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ
Author(s) -
Zhang Jianbo,
Park Sehoon,
Chang Sukbok
Publication year - 2017
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.201708109
Subject(s) - borane , chemistry , steric effects , catalysis , substituent , bond cleavage , cleavage (geology) , in situ , selectivity , silylation , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , materials science , fracture (geology) , composite material
Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers’ borane [(C 6 F 5 ) 2 BH] generated in situ. The hydrosilylative C−O bond cleavage of silyl‐protected mono‐ and disaccharides in the presence of a (C 6 F 5 ) 2 BH catalyst, generated in situ from (C 6 F 5 ) 2 BOH, takes place with excellent chemo‐ and regioselectivities to provide a range of polyols. A study of the substituent effects of sugars on the catalytic activity and selectivity revealed that the steric environment around the anomeric carbon (C1) is crucial.