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金催化的手性偕丙基磺酰胺的分子间氧化:一种获得手性富集吡咯烷-3-酮的可靠方法。

Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: a reliable access to enantioenriched pyrrolidin-3-ones.

机构信息

State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, Fujian, PR China.

出版信息

Chem Commun (Camb). 2014 Mar 7;50(19):2522-5. doi: 10.1039/c3cc49238a. Epub 2014 Jan 24.

Abstract

A gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides has been developed, which provides a reliable access to synthetically useful chiral pyrrolidin-3-ones with excellent ee, by combining the chiral tert-butylsulfinimine chemistry and gold catalysis. This methodology has also been used in the facile synthesis of natural product (-)-irniine. The use of readily available starting materials, a broad substrate scope, a simple procedure and the mild nature of this reaction render it a viable alternative for the synthesis of enantioenriched pyrrolidin-3-ones.

摘要

一种金催化的手性偕丙基磺酰胺的分子间氧化反应已被开发出来,它将手性叔丁基亚磺酰胺化学和金催化结合起来,为合成具有优异对映选择性的手性吡咯烷-3-酮提供了一种可靠的方法,具有很好的应用价值。该方法还用于天然产物(-)-irniine 的简便合成。该反应使用易得的起始原料、广泛的底物范围、简单的操作步骤和温和的反应条件,为手性吡咯烷-3-酮的合成提供了一种可行的替代方法。

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