A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center.
[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.
Tokuda
Osamu
O
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Japan.
Kano
Taichi
T
Gao
Wei-Guo
WG
Ikemoto
Tetsuya
T
Maruoka
Keiji
K
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D006016:Glycolates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D003510:Cyclohexanes; D006016:Glycolates; D002244:Carbon; C512920:(S)-2-cyclohexyl-2-phenylglycolic acid