2,2-二甲基-1-芳基-1-茚醇中立体动态和立体不稳定对映异构体的绝对构型。

Stereodynamics and absolute configuration of stereolabile atropisomers in 2,2-dimethyl-1-aryl-1-indanols.

机构信息

Department of Chemistry, University of Basilicata, via dell'Ateneo Lucano 10, Potenza 85100, Italy.

出版信息

Chirality. 2011 Oct;23(9):768-78. doi: 10.1002/chir.20988. Epub 2011 Aug 18.

DOI:10.1002/chir.20988

Abstract

We describe herein the investigation of the stereodynamic processes occurring in a series of 1-aryl-2,2-dimethylindanols, by dynamic NMR. When the aryl moiety is a mesityl or a 2-methyl-1-naphthyl, the rotational barrier exceeds the 25 kcal/mol, so that stable atropisomers are observed. In two cases, all the chiral-atropisomeric species have been separated by enantioselective HPLC, and the comparison between theoretical and experimental electronic circular dichroism spectra allowed the absolute configuration assignment of all the isolated species to be obtained.

摘要

我们通过动态 NMR 研究了一系列 1-芳基-2,2-二甲基茚醇中发生的立体动力学过程。当芳基部分为均三甲苯基或 2-甲基-1-萘基时，旋转势垒超过 25 kcal/mol，因此可以观察到稳定的对映体。在两种情况下，所有手性对映异构体都通过对映选择性 HPLC 进行了分离，并通过理论和实验电子圆二色性光谱的比较，获得了所有分离物种的绝对构型分配。