基于吡喃葡萄糖苷的双（恶唑啉） - 立体、构型和构象对立体选择性的影响。

Bis(oxazolines) based on glycopyranosides - steric, configurational and conformational influences on stereoselectivity.

机构信息

Institute of Organic Chemistry, Gottfried-Wilhelm-Leibniz University of Hannover, Schneiderberg 1B, D-30167 Hannover, Germany.

出版信息

Beilstein J Org Chem. 2010 Mar 4;6:23. doi: 10.3762/bjoc.6.23.

DOI:10.3762/bjoc.6.23

PMID:20502606

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2874406/

Abstract

In previous studies we found that the asymmetric induction of bis(oxazolines) based on D-glucosamine strongly depended on the steric demand of the 3-O-substituents. To further probe the impact of the 3-position of the pyranose scaffold, we prepared 3-epimerised and 3-defunctionalised versions of these ligands as well as a 3-O-formyl derivative. Application of these new ligands in asymmetric cyclopropanation revealed strong steric and configurational effects of position 3 on asymmetric induction, further dramatic effects of the pyranose conformation were also observed.

摘要

在之前的研究中，我们发现基于 D-葡萄糖胺的双恶唑啉的不对称诱导强烈依赖于 3-O-取代基的空间需求。为了进一步探究吡喃糖骨架 3-位的影响，我们制备了这些配体的 3-差向异构体和 3-去功能化版本，以及一个 3-O-甲酰基衍生物。这些新配体在不对称环丙烷化中的应用揭示了 3 位对不对称诱导的强烈空间和构象效应，同时也观察到吡喃糖构象的显著影响。