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一种通过形成新型环状次膦酸来分离双(α-羟烷基)次膦酸非对映异构体的新方法。

A novel method for the separation of bis(alpha-hydroxyalkyl)phosphinic acid diastereoisomers via formation of novel cyclic phosphinic acids.

作者信息

Kaboudin Babak, Haghighat Hamideh, Yokomatsu Tsutomu

机构信息

Department of Chemistry, Institute for Advanced Studies in Basic Sciences, Gava Zang, Zanjan 45195-1159, Iran.

出版信息

J Org Chem. 2006 Aug 18;71(17):6604-6. doi: 10.1021/jo060547h.

DOI:10.1021/jo060547h
PMID:16901151
Abstract

The reaction of aromatic and aliphatic aldehydes with hypophosphorus acid under microwave irradiation was examined. The reaction gave a mixture of a racemic pair of bis(alpha-hydroxyalkyl)phosphinic acids and acetal derivatives from the corresponding bis(alpha-hydroxyalkyl)phosphinic acids of meso-stereochemistry in good yield. The difference in solubility in organic solvents due to polarity allowed us to readily separate these compounds. This method constitutes an easy, rapid, and good-yielding preparation and separation of bis(alpha-hydroxyalkyl) phosphinic acid diastereoisomers from simple starting materials using microwave irradiation.

摘要

研究了芳香醛和脂肪醛在微波辐射下与次磷酸的反应。该反应得到了一对外消旋的双(α-羟烷基)次膦酸混合物以及来自相应内消旋立体化学的双(α-羟烷基)次膦酸的缩醛衍生物,产率良好。由于极性导致在有机溶剂中的溶解度差异,使我们能够轻松分离这些化合物。该方法构成了一种使用微波辐射从简单起始原料中简便、快速且高产率地制备和分离双(α-羟烷基)次膦酸非对映异构体的方法。

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