Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Anomeric Hydroxyl Groups and a Controlled Reduction of the Glycosyl Ester Products

A catalytic method is developed for the diastereoselective acylation of the anomeric hydroxyl group in diverse carbohydrates to form either α- or β-anomeric esters. While exclusive formation of the β-isomer was observed in most sugar substrates with one enantiomer of the chiral catalyst, moderate to...

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Bibliographic Details
Published in:Organic letters 2017-02, Vol.19 (3), p.508-511
Main Authors: Wang, Hao-Yuan, Simmons, Christopher J, Zhang, Yu, Smits, Angela M, Balzer, Paul G, Wang, Shuojin, Tang, Weiping
Format: Article
Language:English
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Summary:A catalytic method is developed for the diastereoselective acylation of the anomeric hydroxyl group in diverse carbohydrates to form either α- or β-anomeric esters. While exclusive formation of the β-isomer was observed in most sugar substrates with one enantiomer of the chiral catalyst, moderate to high α-selectivity was obtained by using the other enantiomer of the chiral catalyst. The resulting α- and β-anomeric esters have very different reactivity toward a reduction reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03683