通过四取代碳中心的有机催化不对称构建实现(S)-2-环己基-2-苯基乙醇酸的实用合成。

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

作者信息

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

机构信息

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

出版信息

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

DOI:10.1021/ol052164w

PMID:16235968

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.

摘要

[反应：见正文] 报道了一种简洁且对映选择性合成（S）-2-环己基-2-苯基乙醇酸的方法，其为（S）-奥昔布宁的关键中间体。在温和条件下，通过脯氨酸催化环己酮与苯乙醛酸乙酯之间的直接不对称羟醛反应，以优异的立体选择性构建了关键的不对称四取代碳中心。