Synthesis and structure of a chiral areno-bridged [2.4]metacyclophane

被引：6

作者：

Akther, Thamina ^{[1
]}

Islam, Md. Monarul ^{[1
,2
]}

Matsumoto, Taisuke ^{[3
]}

Tanaka, Junji ^{[3
]}

Thuery, Pierre ^{[4
]}

Redshaw, Carl ^{[5
]}

Yamato, Takehiko ^{[1
]}

机构：

[1] Saga Univ, Fac Sci & Engn, Dept Appl Chem, Honjo Machi 1, Saga 8408502, Japan

[2] BCSIR, Chem Res Div, Dhaka 1205, Bangladesh

[3] Kyushu Univ, Inst Mat Chem & Engn, 6-1 Kasugakoen, Kasuga, Fukuoka 8168580, Japan

[4] Univ Paris Saclay, CEA Saclay, CNRS, NIMBE,CEA, F-91191 Gif Sur Yvette, France

[5] Univ Hull, Sch Math & Phys Sci, Dept Chem, Cottingham Rd, Kingston Upon Hull HU6 7RX, Yorks, England

来源：

TETRAHEDRON | 2018年 / 74卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

Metacyclophane; McMurry reaction; Bromination; Diels-Alder reaction; Chirality; MEDIUM-SIZED CYCLOPHANES; LOW-VALENT TITANIUM; SKIPPED CYCLIC ENEDIYNES; DIELS-ALDER REACTIONS; OPTICAL RESOLUTION; CIRCULAR-DICHROISM; COUPLING REACTIONS; CONVERSION; CONFORMATIONS; SUBSTITUENTS;

D O I：

10.1016/j.tet.2017.11.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reductive coupling reaction of 1,4-bis(3-acetyl-5-tert-butyl-2-methoxyphenyl)butane 3 was carried out using TiCl4-Zn in pyridine followed by a McMurry coupling reaction to afford the compounds anti and syn 1,2-dimethyl[2.4]MCP-1-ene 4. Bromination of 4 with BTMA-Br-3 in dry CH2Cl2 afforded the interesting compound 1,2-bis-(bromomethyl)-5,15-di-tert-buty1-8,18-dimethoxy[2.4]MCP-1-ene 6 and consecutive debromination with Zn and AcOH in CH2Cl2 solution afforded the stable solid 5,15-di-tert-butyl-8,18-dimethoxy-1,2-dimethylene[2.4]MCP 7 in 89% yield. Compound 7 was conveniently employed in a Diels Alder reaction with dimethyl acetylenedicarboxylate (DMAD) to provide 2-(3',6'-dihydrobenzo)-5,15-di-tert-butyl-8,18-dimethoxy[2.4]MCP-4',5'-dimethylcarboxylate 8 in good yield. Diels Alder adduct 8 was converted into a novel and inherently chiral areno-bridged compound [2.4]MCP 9 by aromatization. The chirality of the two conformers was characterized by circular dichroism (CD) spectra of the separated enantiomer which are perfect mirror images of each other. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：329 / 335

页数：7

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