Synthesis of C2-Symmetric bisamidines:: A new type of chiral metal-free lewis acid analogue interacting with carbonyl groups

被引：47

作者：

Akalay, Deniz ^{[1
]}

Duerner, Gerd ^{[1
]}

Bats, Jan W. ^{[1
]}

Bolte, Michael ^{[1
]}

Goebel, Michael W. ^{[1
]}

机构：

[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期

关键词：

D O I：

10.1021/jo070534j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral bisamidine 5 has been prepared in just two steps from malonodinitrile. In the monocationic form this compound adopts a planar conformation with an almost convergent orientation of two N-H groups. Ketones, aldehydes, and nitro compounds are assumed to bind to this strongly polar cleft via hydrogen bonds, resulting in a Lewis-acid-like activation of the carbonyl groups. A broad scope of reactions (Diels-Alder, hetero-Diels-Alder, Friedel-Crafts) can be catalyzed. The observed accelerations surpass the rate effects of neutral hydrogen-bond donors such as thioureas or TADDOLs.

引用

页码：5618 / 5624

页数：7

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