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手性膦酸酯和次膦酸酯与胺和醇的立体选择性偶联:一种制备光学活性有机磷酰酸衍生物的通用方法。

Stereospecific coupling of H-phosphinates and secondary phosphine oxides with amines and alcohols: a general method for the preparation of optically active organophosphorus acid derivatives.

机构信息

Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, China.

出版信息

J Org Chem. 2010 Jun 4;75(11):3890-2. doi: 10.1021/jo100473s.

Abstract

The reaction of H-phosphinates and secondary phosphine oxides with amines and alcohols proceeds highly stereospecifically to give the corresponding coupling products with inversion of configuration at the phosphorus center under the Atherton-Todd reaction conditions. This finding leads to the establishment of a general and efficient method for the synthesis of a variety of optically active organophosphorus acid derivatives from the easily available chiral H-phosphinates and secondary phosphine oxides.

摘要

在 Atherton-Todd 反应条件下,H-膦酸酯和仲膦氧化物与胺和醇反应高度立体特异性,在磷中心构型反转的情况下得到相应的偶联产物。这一发现为从易得的手性 H-膦酸酯和仲膦氧化物合成各种光学活性有机磷酸衍生物提供了一种通用且高效的方法。

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