Terpene cyclization catalysis with a functional cavitand: driving selectivity through precise molecular recognition

IF 4.7 1区 化学 Q1 CHEMISTRY, ORGANIC
Ricard López-Coll, Agustí Lledó
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引用次数: 0

Abstract

A three-walled self-folding cavitand receptor derived from resorcin[4]arene featuring phenol groups near the confined space catalyzes the cyclization reaction of nerol, using HCl as co-catalyst. In contrast to terpene cyclization reactions mediated by other synthetic hosts, the process reported herein is substrate specific, provides very high selectivity towards cyclization products, and delivers limonene—a thermodynamically disfavored product—as the major compound. The observed acceleration, turnover and unique selectivity are rationalized on the basis of precise molecular recognition phenomena, supported by NMR studies and DFT calculations.
用功能空腔催化萜烯环化:通过精确分子识别驱动选择性
间苯二酚[4]芳烃衍生的三壁自折叠腔体受体在受限空间附近具有苯酚基团,以HCl为助催化剂催化了间苯二酚的环化反应。与其他合成宿主介导的萜烯环化反应相比,本文报道的过程具有底物特异性,对环化产物提供了非常高的选择性,并提供了柠檬烯-一种热力学上不受欢迎的产物-作为主要化合物。在核磁共振研究和DFT计算的支持下,基于精确的分子识别现象,对观察到的加速、周转和独特的选择性进行了合理化。
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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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