Self-Assembled Supramolecular Structures as Catalysts for Reactions Involving Cationic Transition States

被引：31

作者：

Catti, Lorenzo ^{[1
]}

Zhang, Qi ^{[1
]}

Tiefenbacher, Konrad ^{[1
]}

机构：

[1] Tech Univ Munich, Dept Chem, Lichtenbergstr 4, D-85747 Garching, Germany

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 03期

关键词：

catalysis; supramolecular chemistry; carbocation; self-assembly; enzyme mimicry; HEXAMERIC RESORCINARENE CAPSULE; AZA-COPE REARRANGEMENT; METAL-LIGAND CLUSTER; BASIC SOLUTION; NAZAROV CYCLIZATION; DIFFUSION NMR; REVERSIBLE ENCAPSULATION; ORTHOFORMATE HYDROLYSIS; TERPENE BIOSYNTHESIS; MECHANISTIC INSIGHTS;

D O I：

10.1055/s-0035-1560362

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Self-assembled supramolecular structures represent easily accessible systems for the study of enzyme-like catalysis. The hydrophobic cavities of the assemblies provide a distinct chemical environment that can lead to unusual chemo-and stereoselectivities. This review summarizes the application of such host structures in the catalysis of reactions involving cationic transition states and includes detailed discussion of mechanisms and substrate-host interactions. The literature up to April 2015 is covered. 1 Introduction 2 Molecular Capsules: Structures and Background 3 Catalyzed Reactions 4 Summary and Outlook

引用

页码：313 / 328

页数：16

共 77 条

[1] Encapsulation Studies of Cationic Gold Complexes within a Self-Assembled Hexameric Resorcin[4]arene Capsule [J].

Adriaenssens, Louis ;

Escribano-Cuesta, Ana ;

Homs, Anna ;

Echavarren, Antonio M. ;

Ballester, Pablo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (08) :1494-1500

[2]

Albrecht M, 2012, TOP CURR CHEM, V319, pIX

[3] Hydrogen-bonded molecular capsules are stable in polar media [J].

Atwood, JL ;

Barbour, LJ ;

Jerga, A .

CHEMICAL COMMUNICATIONS, 2001, (22) :2376-2377

[4] Self-recognition, structure, stability, and guest affinity of pyrogallol[4]arene and resorcin[4]arene capsules in solution [J].

Avram, L ;

Cohen, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) :11556-11563

[5] Hexameric capsules of lipophilic pyrogallolarene and resorcinarene in solutions as probed by diffusion NMR: One hydroxyl makes the difference [J].

Avram, L ;

Cohen, Y .

ORGANIC LETTERS, 2003, 5 (18) :3329-3332

[6] Spontaneous formation of hexameric resorcinarene capsule in chloroform solution as detected by diffusion NMR [J].

Avram, L ;

Cohen, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15148-15149

[7] Efficient isonitrile hydration through encapsulation within a hexameric self-assembled capsule and selective inhibition by a photo-controllable competitive guest [J].

Bianchini, Giulio ;

La Sorella, Giorgio ;

Canever, Nicolo ;

Scarso, Alessandro ;

Strukul, Giorgio .

CHEMICAL COMMUNICATIONS, 2013, 49 (46) :5322-5324

[8] The hydrophobic effect drives the recognition of hydrocarbons by an anionic metal-ligand cluster [J].

Biros, Shannon M. ;

Bergman, Robert G. ;

Raymond, Kenneth N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) :12094-+

[9] Supramolecular Catalysis in Metal-Ligand Cluster Hosts [J].

Brown, Casey J. ;

Toste, F. Dean ;

Bergman, Robert G. ;

Raymond, Kenneth N. .

CHEMICAL REVIEWS, 2015, 115 (09) :3012-3035

[10] Enantioselective Catalysis of the Aza-Cope Rearrangement by a Chiral Supramolecular Assembly [J].

Brown, Casey J. ;

Bergman, Robert G. ;

Raymond, Kenneth N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (48) :17530-17531

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