使用手性金属有机框架作为可回收多相催化剂，环氧化合物与芳香胺的不对称开环反应。

Asymmetric ring-opening reaction of -epoxides with aromatic amines using homochiral metal-organic frameworks as recyclable heterogeneous catalysts.

作者信息

Tanaka Koichi, Kinoshita Maya, Kayahara Jun, Uebayashi Yutaro, Nakaji Kazusada, Morawiak Maja, Urbanczyk-Lipkowska Zofia

机构信息

Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University Suita Osaka 564-8680 Japan

Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52 01-224 Warszawa Poland

出版信息

RSC Adv. 2018 Aug 6;8(49):28139-28146. doi: 10.1039/c8ra05163a. eCollection 2018 Aug 2.

DOI:10.1039/c8ra05163a

PMID:35542745

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9083937/

Abstract

An efficient asymmetric ring-opening (ARO) reaction of -epoxides with aromatic amines catalysed by a series of homochiral metal-organic frameworks (MOFs) was carried out. Excellent results (up to 95% ee) for the ARO of cyclohexene oxide with several aromatic amines were achieved with a homochiral MOF derived from the ligand ()-2,2'-dihydroxyl-1,1'-binaphthalene-5,5'-dicarboxylic acid. Furthermore, homochiral MOFs based on ()-2,2'-dihydroxy-1,1'-binaphthyl-4,4'-di(4-benzoic acid) and ()-2,2'-diethoxy-1,1'-binaphthyl-4,4'-di(5-isophthalic acid) catalysed ARO reactions of -stilbene oxide with 1-naphthylamine in high yield (up to 95%) and excellent enantioselectivity (up to 97%) of the β-amino alcohol. The MOF catalysts were recoverable and recyclable with retention of their performance.

摘要

进行了一系列手性金属有机骨架（MOF）催化的环氧化合物与芳香胺的高效不对称开环（ARO）反应。使用源自配体（）-2,2'-二羟基-1,1'-联萘-5,5'-二羧酸的手性MOF，实现了环氧环己烷与几种芳香胺的ARO反应的优异结果（对映体过量高达95%）。此外，基于（）-2,2'-二羟基-1,1'-联萘基-4,4'-二（4-苯甲酸）和（）-2,2'-二乙氧基-1,1'-联萘基-4,4'-二（5-间苯二甲酸）的手性MOF催化了氧化芪与1-萘胺的ARO反应，β-氨基醇的产率高（高达95%）且对映选择性优异（高达97%）。MOF催化剂可回收且可循环使用，并保持其性能。