通过 Sharpless 不对称双羟化反应对 p-苯基苄基巴豆酸酯进行对映体纯的 syn-2,3-二羟基丁酸的可扩展合成。
Scalable synthesis of enantiomerically pure syn-2,3-dihydroxybutyrate by Sharpless asymmetric dihydroxylation of p-phenylbenzyl crotonate.
机构信息
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
出版信息
J Org Chem. 2011 Oct 21;76(20):8554-9. doi: 10.1021/jo2016746. Epub 2011 Sep 22.
Abstract
An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.
摘要
详细描述了一种高效的四步合成路线，用于制备具有>95%ee 值的有用手性砌块（2R，3S）-二羟基丁酸缩酮。该序列易于放大，无需层析，并且允许有效回收对苯基苄醇，这是通过重结晶实现对映体和非对映体富集的简便方法。
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