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固有手性杯芳烃:合成、光学拆分、手性识别及不对称催化

Inherently chiral calixarenes: synthesis, optical resolution, chiral recognition and asymmetric catalysis.

作者信息

Li Shao-Yong, Xu Yao-Wei, Liu Jun-Min, Su Cheng-Yong

机构信息

College of Pharmacy, Tianjin Medical University, Tianjin 300070, China; E-Mail:

出版信息

Int J Mol Sci. 2011 Jan 17;12(1):429-55. doi: 10.3390/ijms12010429.

DOI:10.3390/ijms12010429
PMID:21339996
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3039962/
Abstract

Inherently chiral calixarenes, whose chirality is based on the absence of a planar symmetry or an inversion center in the molecules as a whole through the asymmetric array of several achiral groups upon the three-dimensional calix-skeletons, are challenging and attractive chiral molecules, because of their potential in supramolecular chemistry. The synthesis and optical resolution of all varieties of inherently chiral calixarenes are systematically discussed and classified, and their applications in chiral recognition and asymmetric catalysis are thoroughly illustrated in this review.

摘要

固有手性杯芳烃是具有挑战性且极具吸引力的手性分子,其手性基于整个分子中不存在平面对称性或反演中心,这是通过三维杯状骨架上几个非手性基团的不对称排列实现的。由于其在超分子化学中的潜力,本文对各种固有手性杯芳烃的合成和光学拆分进行了系统的讨论和分类,并详细阐述了它们在手性识别和不对称催化中的应用。

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本文引用的文献

1
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2
An asymmetric ortholithiation approach to inherently chiral calix[4]arenes.一种用于合成固有手性杯[4]芳烃的不对称邻位锂化方法。
Org Lett. 2009 Nov 5;11(21):4986-9. doi: 10.1021/ol902238p.
3
Synthesis and resolution of a multifunctional inherently chiral calix[4]arene with an ABCD substitution pattern at the wide rim: the effect of a multifunctional structure in the organocatalyst on enantioselectivity in asymmetric reactions.
通过手性硫化物催化的去对称芳基亚磺酰化反应对固有手性含硫杯[4]芳烃进行对映选择性合成。
Nat Commun. 2024 Nov 15;15(1):9929. doi: 10.1038/s41467-024-54380-1.
4
Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes.通过钴催化杯[4]芳烃的对映选择性C-H活化同时构建固有手性和轴手性
Nat Commun. 2024 Sep 3;15(1):7673. doi: 10.1038/s41467-024-52133-8.
5
synthesis of inherently chiral heteracalix[4]aromatics from enantioselective macrocyclization enabled by chiral phosphoric acid-catalyzed intramolecular SAr reaction.通过手性磷酸催化的分子内亲核芳香取代反应实现对映选择性大环化,从而合成固有手性杂杯[4]芳烃。
Chem Sci. 2024 Jan 26;15(10):3610-3615. doi: 10.1039/d3sc06436k. eCollection 2024 Mar 6.
6
Bioinspired Framework Catalysts: From Enzyme Immobilization to Biomimetic Catalysis.仿生框架催化剂:从酶固定化到仿生催化。
Chem Rev. 2023 May 10;123(9):5347-5420. doi: 10.1021/acs.chemrev.2c00879. Epub 2023 Apr 12.
7
The Use of Anhydrous Barium Hydroxide for Selective Alkylation of Dialkyloxy--butyl-calix[4]arenes.无水氢氧化钡在选择性二烷氧基丁基杯[4]芳烃烷基化反应中的应用。
Molecules. 2023 Jan 21;28(3):1089. doi: 10.3390/molecules28031089.
8
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9
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Molecules. 2022 Dec 4;27(23):8545. doi: 10.3390/molecules27238545.
10
Highly functionalized calix[4]arenes multicomponent reactions: synthesis and recognition properties.高官能化杯[4]芳烃多组分反应:合成与识别性能
RSC Adv. 2019 Jun 24;9(34):19596-19605. doi: 10.1039/c9ra03354h. eCollection 2019 Jun 19.
一种在宽环上具有ABCD取代模式的多功能固有手性杯[4]芳烃的合成与拆分:有机催化剂中多功能结构对不对称反应对映选择性的影响。
J Org Chem. 2009 Feb 6;74(3):1288-96. doi: 10.1021/jo8024412.
4
Selective hetero-trisfunctionalization of the large rim of a biomimetic calix[6]arene using host-guest chemistry as a synthetic tool.利用主客体化学作为合成工具,对仿生杯[6]芳烃大环进行选择性异三官能化。
J Am Chem Soc. 2008 Nov 19;130(46):15226-7. doi: 10.1021/ja803878g. Epub 2008 Oct 25.
5
Novel chiral calix[4]arenes by direct asymmetric epoxidation reaction.通过直接不对称环氧化反应合成新型手性杯[4]芳烃
J Org Chem. 2008 Jun 6;73(11):4233-6. doi: 10.1021/jo800301m. Epub 2008 Apr 24.
6
Effective nonenzymatic kinetic resolution of racemic m-nitro-substituted inherently chiral aminocalix[4]arenes.外消旋间硝基取代的固有手性氨基杯[4]芳烃的有效非酶动力学拆分
Org Lett. 2008 Feb 7;10(3):477-9. doi: 10.1021/ol702884u. Epub 2008 Jan 10.
7
A new approach to enantiopure inherently chiral calix[4]arenes: determination of their absolute configurations.对映体纯的固有手性杯[4]芳烃的一种新方法:其绝对构型的测定。
Org Lett. 2007 Oct 25;9(22):4447-50. doi: 10.1021/ol701714q. Epub 2007 Sep 26.
8
Design of a novel inherently chiral calix[4]arene for chiral molecular recognition.用于手性分子识别的新型固有手性杯[4]芳烃的设计
Org Lett. 2007 Aug 2;9(16):3117-9. doi: 10.1021/ol071249p. Epub 2007 Jul 6.
9
Diastereoselective lower rim (1S)-camphorsulfonylation as the shortest way to the inherently chiral calix[4]arene.非对映选择性的下边缘(1S)-樟脑磺酰化反应是合成固有手性杯[4]芳烃的最短途径。
Org Lett. 2007 Mar 29;9(7):1183-5. doi: 10.1021/ol0628513. Epub 2007 Feb 27.
10
Calix[4]arene alpha-aminophosphonic acids: asymmetric synthesis and enantioselective inhibition of an alkaline phosphatase.杯[4]芳烃α-氨基膦酸:碱性磷酸酶的不对称合成及对映选择性抑制
Org Lett. 2006 Feb 16;8(4):549-52. doi: 10.1021/ol052469a.