Recognition-mediated facilitation of a disfavored Diels-Alder reaction

被引：25

作者：

Bennes, R ^{[1
]}

Philp, D ^{[1
]}

Spencer, N ^{[1
]}

Kariuki, BM ^{[1
]}

Harris, KDM ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 07期

关键词：

D O I：

10.1021/ol9908880

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The rational design of a system which is capable of accelerating and facilitating a thermodynamically disfavored Diets-Alder cycloaddition between a furan and a maleimide is presented. The origins of the acceleration and facilitation of the cycloaddition reaction are traced by kinetic studies-allied to results from H-1 NMR spectroscopy and X-ray crystallography-to the formation of strong intramolecular hydrogen bonds in the cycloadduct.

引用

页码：1087 / 1090

页数：4

共 35 条

[1] Efficient recognition-induced acceleration of a [3+2] dipolar cycloaddition reaction [J].

Booth, CA ;

Philp, D .

TETRAHEDRON LETTERS, 1998, 39 (38) :6987-6990

[2] AN ANTIBODY-CATALYZED BIMOLECULAR DIELS-ALDER REACTION [J].

BRAISTED, AC ;

SCHULTZ, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7430-7431

[3] BIOMIMETIC CHEMISTRY AND ARTIFICIAL ENZYMES - CATALYSIS BY DESIGN [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :146-153

[4] THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

BRIEGER, G ;

BENNETT, JN .

CHEMICAL REVIEWS, 1980, 80 (01) :63-97

[5] Ground state and transition state contributions to the rates of intramolecular and enzymatic reactions [J].

Bruice, TC ;

Lightstone, FC .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (02) :127-136

[6]

Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01

[7] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

CRAIG, D .

CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238

[8] Harvesting Diels and Alder's garden: Synthetic investigations of intramolecular [4+2] cycloadditions [J].

Fallis, AG .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (06) :464-474

[9] THE INTRAMOLECULAR DIELS-ALDER REACTION - RECENT ADVANCES AND SYNTHETIC APPLICATIONS [J].

FALLIS, AG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02) :183-234

[10] CONTROL OF THE EXO-PATHWAY AND ENDO-PATHWAY OF THE DIELS-ALDER REACTION BY ANTIBODY CATALYSIS [J].

GOUVERNEUR, VE ;

HOUK, KN ;

DEPASCUALTERESA, B ;

BENO, B ;

JANDA, KD ;

LERNER, RA .

SCIENCE, 1993, 262 (5131) :204-208

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