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
收藏
页码：917 / 919
页数：3
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