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首页> 外文期刊>ACS Omega >Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride
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Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride

机译：外消旋α-羟基膦酸酯的拆分：Bi（OTf）3-催化的（+）-二苯甲酰基-1-酒石酸酐对α-羟基膦酸酯的立体选择性酯化

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摘要

A practical and efficient method has been developed for the preparation of optically active α-hydroxyphosphonates through resolution of the racemates. Treatment of racemic diethyl 1-hydroxy-1-phenylmethylphosphonate (1) with (+)-dibenzoyl-L-tartaric anhydride gave two diastereomeric esters 2 and 3 in the presence of bismuth triflate (15 mol %) in an 86:14 ratio. The two diastereomeric esters were separated by simple column chromatography, and the structure for the major diastereomer was determined by X-ray crystallographic analysis. Simple hydrolysis of the isolated major diastereomer in the usual manner afforded (R)-O,O-diethyl-1-[hydroxyl(phenyl)methyl] phosphonate 1. The advantages of the present method are that the operation is simple and easy to handle, along with rapid and good yield preparations of both enantiomers of the racemic α-phosphonates 1. Diastereoselective reactions of various racemic α-hydroxyphosphonates with d-Bz-L-TA in the presence of Bi(OTf)3 are also described.
机译：通过消旋体的拆分，已开发出一种实用而有效的方法来制备旋光性α-羟基膦酸酯。用（+）-二苯甲酰基-L-酒石酸酐处理外消旋的1-羟基-1-苯基甲基膦酸二乙酯（1），在三氟甲磺酸铋（15摩尔％）的存在下以86∶14的比例得到两种非对映体酯2和3。通过简单的柱色谱法分离两种非对映体酯，并通过X射线晶体学分析确定主要非对映体的结构。以通常的方式将分离的主要非对映异构体简单水解，得到（R）-O，O-二乙基-1- [羟基（苯基）甲基]膦酸酯1。本方法的优点是操作简单且易于处理还描述了外消旋α-膦酸酯的两种对映异构体的快速，高收率的制备方法。还描述了在Bi（OTf）3存在下，各种外消旋α-羟基膦酸酯与d-Bz-L-TA的非对映选择性反应。

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