title: Iridium-Catalyzed Dynamic Kinetic Isomerization: Expedient Synthesis of Carbohydrates from Achmatowicz Rearrangement Products.
abstract: A highly stereoselective dynamic kinetic isomerization of Achmatowicz rearrangement products was discovered. This new internal redox isomerization provided ready access to key intermediates for the enantio- and diastereoselective synthesis of a series of naturally occurring sugars. The nature of the de novo synthesis also enables the preparation of both enantiomers.
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA).
authors.forename: Hao-Yuan
authors.initials: HY
authors.lastname: Wang
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA).
authors.forename: Ka
authors.initials: K
authors.lastname: Yang
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA).
authors.forename: Scott R
authors.initials: SR
authors.lastname: Bennett
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA). guosr9609@lsu.edu.cn.|Department of Chemistry, Lishui University, Lishui, Zhejiang Province, 331200 (P.R. China). guosr9609@lsu.edu.cn.
authors.forename: Sheng-rong
authors.initials: SR
authors.lastname: Guo
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705-2222 (USA). wtang@pharmacy.wisc.edu.|Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706 (USA). wtang@pharmacy.wisc.edu.
authors.forename: Weiping
authors.initials: W
authors.lastname: Tang
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D007536:Isomerism
chemical_list: D002241:Carbohydrates; D007495:Iridium
keywords: carbohydrates; deoxysugars; furans; iridium; isomerization