3 years ago

Selective C−O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ

Selective C−O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ
Sehoon Park, Sukbok Chang, Jianbo Zhang
Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers’ borane [(C6F5)2BH] generated in situ. The hydrosilylative C−O bond cleavage of silyl-protected mono- and disaccharides in the presence of a (C6F5)2BH catalyst, generated in situ from (C6F5)2BOH, 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. Piers’ borane [(C6F5)2BH], generated in situ, is demonstrated to promote the hydrosilylative reduction of sugars, thereby providing a series of linear or cyclic polyols with high chemo- and regioselectivities under mild conditions. Studies of catalytic reactivity and regioselectivity with regard to the C−O bond cleavage with hydrosilanes suggest an importance of the steric environment around the anomeric carbon center of the sugar.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708109

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