A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center

Osamu Tokuda; Taichi Kano; Wei-Guo Gao; Tetsuya Ikemoto; Keiji Maruoka

doi:10.1021/ol052164w

A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center

Org Lett. 2005 Oct 27;7(22):5103-5. doi: 10.1021/ol052164w.

Authors

Osamu Tokuda¹, Taichi Kano, Wei-Guo Gao, Tetsuya Ikemoto, Keiji Maruoka

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Japan.

PMID: 16235968
DOI: 10.1021/ol052164w

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon / chemistry*
Catalysis
Cyclohexanes / chemical synthesis*
Cyclohexanes / chemistry
Glycolates / chemical synthesis*
Glycolates / chemistry
Molecular Structure

Substances

Cyclohexanes
Glycolates
Carbon
(S)-2-cyclohexyl-2-phenylglycolic acid