title: Determination of absolute configuration using kinetic resolution catalysts.
abstract: A new method was developed to assign the absolute configuration of molecules using kinetic resolution catalysts. Secondary alcohols were acylated in the presence of Birman's S-HBTM and R-HBTM catalysts, and the fast-reacting catalyst was identified by NMR analysis of the reaction mixture. A mnemonic was developed to assign configuration based on the identity of the fast-reacting catalyst. The method uses only 1-3 mg of alcohol, and it is more convenient than the Mosher method. The kinetic resolution strategy may be extended to other classes of molecules.
authors.affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine, Irvine, California 92697, USA.
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Wagner
authors.forename: Jonathan G
authors.initials: JG
authors.lastname: David
authors.forename: Scott D
authors.initials: SD
authors.lastname: Rychnovsky
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D008968:Molecular Conformation
chemical_list: D000438:Alcohols