title: Kinetic resolution of secondary alcohols using amidine-based catalysts.
abstract: Kinetic resolution of racemic alcohols has been traditionally achieved via enzymatic enantioselective esterification and ester hydrolysis. However, there has long been considerable interest in devising nonenzymatic alternative methods for this transformation. Amidine-based catalysts (ABCs), a new class of enantioselective acyl transfer catalysts developed in our group, have demonstrated, inter alia, high efficacy in the kinetic resolution of benzylic, allylic, and propargylic secondary alcohols and 2-substituted cycloalkanols, and thus provide a viable alternative to enzymes.
authors.affiliation: Department of Chemistry, Washington University, One Brookings Drive, St. Louis, Missouri 63130, USA.
authors.forename: Ximin
authors.initials: X
authors.lastname: Li
authors.forename: Hui
authors.initials: H
authors.lastname: Jiang
authors.forename: Eric W
authors.initials: EW
authors.lastname: Uffman
authors.forename: Lei
authors.initials: L
authors.lastname: Guo
authors.forename: Yuhua
authors.initials: Y
authors.lastname: Zhang
authors.forename: Xing
authors.initials: X
authors.lastname: Yang
authors.forename: Vladimir B
authors.initials: VB
authors.lastname: Birman
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000578:Amidines / Q000737:chemistry*; D019905:Benzyl Alcohol / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003516:Cycloparaffins / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000578:Amidines; D003516:Cycloparaffins; D020005:Propanols; C006463:allyl alcohol; C028255:propargyl alcohol; D019905:Benzyl Alcohol