New access to 4-aryl[2,2]paracyclophanes by high-pressure Diels-Alder reaction

被引：4

作者：

Minuti, Lucio ^{[1
]}

Barattucci, Anna ^{[2
]}

Bonaccorsi, Paola Maria ^{[2
]}

Siciliano, Carlo ^{[3
]}

Temperini, Andrea ^{[4
]}

机构：

[1] Univ Perugia, Dipartimento Chim Biol & Biotecnol, Via Elce Sotto 8, I-06123 Perugia, Italy

[2] Univ Messina, Dipartimento Sci Chim, Viale F Alcontres 31, I-98166 Messina, Italy

[3] Univ Calabria, Dipartimento Farm & Sci Salute & Nutr, Edificio Polifunz, I-87030 Arcavacata Di Rende, Italy

[4] Univ Perugia, Dipartimento Sci Farmaceut, Via Liceo 1, I-06123 Perugia, Italy

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 08期

关键词：

Paracyclophanes; High pressure; Diels-Alder cycloaddition; Biaryls; Catalysis; ASYMMETRIC CONJUGATE ADDITION; LIGANDS; PLANAR;

D O I：

10.1016/j.tetlet.2016.01.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of novel 4-aryl[2,2]paracyclophanes based on the Diels-Alder reaction of 4-carbomethoxyethynyl[2,2]paracyclophane as the dienophile with methyl-1,3-butadienes is described. Activation of the Diels-Alder reactions by high-pressure (8 kbar) in combination with the Lewis acid EtAICl(2) allows to obtain in good yield and total regioselectivity the cyclohexadienyl-paracyclophane cycloadducts that are converted to the corresponding aryl-paracyclophanes by DDQ oxidation. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：917 / 919

页数：3

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