title: Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Anomeric Hydroxyl Groups and a Controlled Reduction of the Glycosyl Ester Products.
abstract: 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.
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
authors.forename: Hao-Yuan
authors.initials: HY
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Simmons
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
authors.forename: Angela M
authors.initials: AM
authors.lastname: Smits
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
authors.forename: Paul G
authors.initials: PG
authors.lastname: Balzer
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.|School of Pharmacy, Hainan Medical University , Haikou 571199, P. R. China.
authors.forename: Shuojin
authors.initials: S
authors.lastname: Wang
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.|Department of Chemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
authors.forename: Weiping
authors.identifier: 0000-0002-0039-3196
authors.initials: W
authors.lastname: Tang