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首页> 外文期刊>有機合成化学協会誌 >Development and Applications of Novel Chiral Auxiliaries Powerful for Both Enantioresolution and Determination of Absolute Configuration by X-Ray Crystallography
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Development and Applications of Novel Chiral Auxiliaries Powerful for Both Enantioresolution and Determination of Absolute Configuration by X-Ray Crystallography

机译：新型手性助剂的开发与应用强大，对X射线晶体学均对enaliore解决和绝对配置的测定

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摘要

Recently, there is a great demand for various chiral organic compounds with 100% e.e. To obtain enantiopure chiral compounds and to determine their absolution employing chiral auxiliaries. We report here the development and applications of novel chiral auxiliaries powerful for both enantioresolution and determination of absolute configuration. The chiral auxiliary, (1S,2R,4R)-(-)-2,10-camphorsultam 5, is useful for enantioresolution of various carboxylic acids by HPLC on silica gel and also for X-ray crystallographic determination of their absolute configurations. Furthermore, we have succeeded in extension of this strategy to various alcohols by designing a new chiral auxiliary connecting (1S,2R,4R)-2,10-camphorsultam moiety and carboxylic acid group. Namely, chiral phthalic (-)-1 and dichlorophthalic (-)-2 acids were allowed to react with racemic alcohols, and the diastereomeric mixture of esters obtained was separated by HPLC on silica gel. These diastereomers generally crystallized as large prismatic crystals suitable for X-ray diffraction, and their absolute configurations could be determined by the X-ray crystallographic method using the camphor part as the internal reference of absolute configuration. The method using these chiral phthalic and dichlorophthalic acids has been applied to various racemic alcohols to obtain enantiopure alcohols and also to determine their absolute stereochemistry.
机译：最近，对各种手性有机化合物具有100％的细胞有机化合物。为了获得对映进的手性化合物并确定其脱离采用手性助剂。我们在此报告了新型手性助剂的开发和应用，强大的enalioresol解决和绝对配置的测定。手性助剂（1S，2R，4R） - （ - ） - 2,10-樟脑曲5，可用于通过HPLC对硅胶上的各种羧酸的映溶解，以及其绝对构型的X射线晶体测定。此外，我们通过设计新的手性辅助连接（1S，2R，4R）-2,10-樟脑和羧酸基团来成功地将这种策略扩展到各种醇。即，使手性邻苯二甲酸（ - ） - 1和二氯邻苯二甲酸二（ - ） - 2酸与外消旋醇反应，并通过HPLC在硅胶上分离所得酯的非对映异构体混合物。这些非对映异构体通常被结晶，作为适用于X射线衍射的大棱柱晶体，它们的绝对配置可以通过X射线晶体法使用樟脑部分作为绝对构造的内部参考来确定。使用这些手性邻苯二甲酸和二氯邻苯二甲酸的方法已经应用于各种外消旋醇以获得对雌性醇的醇，并确定它们的绝对立体化学。

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