A Switchable [2]Rotaxane Asymmetric Organocatalyst That Utilizes an Acyclic Chiral Secondary Amine

被引：173

作者：

Blanco, Victor ^{[1
]}

Leigh, David A. ^{[1
]}

Marcos, Vanesa ^{[1
]}

Morales-Serna, Jose A. ^{[1
]}

Nussbaumer, Alina L. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 13期

基金：

瑞士国家科学基金会; 英国工程与自然科学研究理事会;

关键词：

ALPHA; BETA-UNSATURATED ALDEHYDES; MICHAEL ADDITION; CATALYSIS; ROTAXANE; LIGHT; AMINOCATALYSIS; NANOSWITCH; 3-STATION; STATION; ADVENT;

D O I：

10.1021/ja501561c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rotaxane-based switchable asymmetric organocatalyst has been synthesized in which the change of the position of the macrocycle reveals or conceals an acyclic, yet still highly effective, chiral organocatalytic group. This allows control over both the rate and stereochemical outcome of a catalyzed asymmetric Michael addition.

引用

页码：4905 / 4908

页数：4

共 67 条

[1] Hydrogen-Bonding in Aminocatalysis: From Proline and Beyond [J].

Albrecht, Lukasz ;

Jiang, Hao ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) :358-368

[2] Applications of asymmetric organocatalysis in medicinal chemistry [J].

Aleman, Jose ;

Cabrera, Silvia .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :774-793

[3] Influence of the Reaction Conditions on the Evolution of the Michael Addition of β-Keto Sulfones to α,β-Unsaturated Aldehydes [J].

Aleman, Jose ;

Marcos, Vanesa ;

Marzo, Leyre ;

Garcia Ruano, Jose Luis .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) :4482-4491

[4] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[5] First asymmetric cascade reaction catalysed by chiral primary aminoalcohols [J].

Arroniz, Carlos ;

Escolano, Carmen ;

Luque, F. Javier ;

Bosch, Joan ;

Amat, Mercedes .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) :5079-5085

[6] Switchable Catalysis with a Light-Responsive Cavitand [J].

Berryman, Orion B. ;

Sather, Aaron C. ;

Lledo, Agusti ;

Rebek, Julius, Jr. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9400-9403

[7] Organocatalysis-after the gold rush [J].

Bertelsen, Soren ;

Jorgensen, Karl Anker .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189

[8] A Rotaxane-Based Switchable Organocatalyst [J].

Blanco, Victor ;

Carlone, Armando ;

Haenni, Kevin D. ;

Leigh, David A. ;

Lewandowski, Bartosz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5166-5169

[9] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones [J].

Brandau, Sven ;

Landa, Aitor ;

Franzen, Johan ;

Marigo, Mauro ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4305-4309

[10] N-Benzyltriazolium as Both Molecular Station and Barrier in [2]Rotaxane Molecular Machines [J].

Busseron, Eric ;

Coutrot, Frederic .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08) :4099-4106

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