Synthesis of 3-aryl-4-methyl-1,2-benzenedisulfonimides, new chiral Bronsted acids. A combined experimental and theoretical study

被引：11

作者：

Barbero, Margherita ^{[1
]}

Bazzi, Stefano ^{[1
]}

Cadamuro, Silvano ^{[1
]}

Di Bari, Lorenzo ^{[2
]}

Dughera, Stefano ^{[1
]}

Ghigo, Giovanni ^{[1
]}

Padula, Daniele ^{[2
]}

Tabasso, Silvia ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Chim Organ, I-10125 Turin, Italy

[2] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

TETRAHEDRON | 2011年 / 67卷 / 32期

关键词：

Atropisomerism; Bronsted acids; Density functional calculations; 3-Arylanthranilic acids; Sulfonimides; CROSS-COUPLING REACTION; MOLECULAR-ORBITAL METHODS; O-BENZENEDISULFONIMIDE; BASIS-SETS; CATALYST; EFFICIENT; SOLVATION; ENERGIES; ALCOHOLS; PHENOLS;

D O I：

10.1016/j.tet.2011.05.127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have recently reported the use, in catalytic amounts, of 1,2-benzenedisulfonimide as a safe Bronsted acid in some acid-catalyzed organic reactions. With the design of new and chiral acid organocatalysts with the structure of 1,2-benzenedisulfonimide in mind, we herein propose a synthesis of 1,2-benzenedisulfonimide derivatives bearing an aryl group in the 3-position with good overall yields. The chirality of these compounds is due to the hindered rotation of the aryl group (atropisomerism). We resolved the atropisomers of one of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5789 / 5797

页数：9

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