title: A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center.
abstract: [reaction: see text] A concise and enantioselective synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid as a key intermediate for (S)-oxybutynin is reported. The crucial asymmetric tetrasubstituted carbon center was constructed with excellent stereoselectivity through the proline-catalyzed direct asymmetric aldol reaction between cyclohexanone and ethyl phenylglyoxylate under mild conditions.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Japan.
authors.forename: Osamu
authors.initials: O
authors.lastname: Tokuda
authors.forename: Taichi
authors.initials: T
authors.lastname: Kano
authors.forename: Wei-Guo
authors.initials: WG
authors.lastname: Gao
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Ikemoto
authors.forename: Keiji
authors.initials: K
authors.lastname: Maruoka
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D006016:Glycolates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D003510:Cyclohexanes; D006016:Glycolates; D002244:Carbon; C512920:(S)-2-cyclohexyl-2-phenylglycolic acid