-隐色烷-B的手性同位素类似物的合成及手性光学性质

Synthesis and Chiroptical Properties of a Chiral Isotopologue of -Cryptophane-B.

作者信息

Brotin Thierry, Daugey Nicolas, Kapitan Josef, Vanthuyne Nicolas, Jean Marion, Jeanneau Erwann, Buffeteau Thierry

机构信息

ENSL, UMR 5182-CNRS, Laboratoire de Chimie, 46 Allée d'Italie, 69364 Lyon, France.

Institut des Sciences Moléculaires (UMR 5255-CNRS), Université de Bordeaux, 351 Cours de la Libération, 33405 Talence, France.

出版信息

J Org Chem. 2023 Apr 7;88(7):4829-4832. doi: 10.1021/acs.joc.2c03101. Epub 2023 Mar 20.

DOI:10.1021/acs.joc.2c03101

PMID:36940313

Abstract

We report the synthesis and absolute configuration (AC) of a chiral isotopologue of -cryptophane-B. Low chiral signatures were measured by polarimetry and electronic circular dichroism, whereas most significant chiroptical effects were observed by vibrational circular dichroism (VCD) and Raman optical activity (ROA). The comparison of experimental VCD and ROA spectra with those predicted by DFT calculations allows the determination of the AC of the two enantiomers as (-)--- and (+)---.

摘要

我们报道了一种手性同位素体-隐色体-B的合成及绝对构型（AC）。通过旋光法和电子圆二色性测量得到了较低的手性特征，而通过振动圆二色性（VCD）和拉曼光学活性（ROA）观察到了最显著的手性光学效应。将实验VCD和ROA光谱与密度泛函理论（DFT）计算预测的光谱进行比较，可确定两种对映体的AC分别为（-）---和（+）---。