Recognition-induced control of a Diels-Alder cycloaddition

被引：44

作者：

Robertson, A ^{[1
]}

Philp, D ^{[1
]}

Spencer, N ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1999年 / 55卷 / 37期

基金：

英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;

关键词：

furans; cycloaddition; kinetics; molecular recognition;

D O I：

10.1016/S0040-4020(99)00633-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rational design of systems which are capable of accelerating and/or controlling the stereochemical outcome of the Diels-Alder cycloaddition reaction between a furan and a maleimide is presented. The origins of the acceleration and control of the cycloaddition reactions are traced by kinetic studies - allied to molecular mechanics calculations - to the formation of complexes in which the dienes and the dieneophiles are placed in the appropriate arrangements for reaction, and, more importantly, to the formation of intramolecular hydrogen bonds in the cycloadducts. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11365 / 11384

页数：20

共 46 条

[11] Remote regiocontrol by a thioether group in Diels-Alder reactions of naphthazarin: Regioselective access to tetracyclic polyhydroxyquinones [J].

Carreno, MC ;

Ruano, JLG ;

Urbano, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6136-6138

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

CRAIG, D .

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

[13] 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

[14]

FALLIS AG, IN PRESS ACC CHEM RE

[15]

GIGANEK E, 1984, ORG REACTIONS, V32, P1

[16] HYDROXAMIC ACIDS .6. SYNTHESIS, PROPERTIES AND REACTIONS OF AMIDIC HYDROXAMIC ACID AND DIHYDROXAMIC ACID-DERIVATIVES [J].

HEARN, MTW ;

WARD, AD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (09) :2031-2043

[17] COMPLEXATION CONTROL OF PERICYCLIC-REACTIONS - SUPRAMOLECULAR EFFECTS ON THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

HIRST, SC ;

HAMILTON, AD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :382-383

[18] SUPRAMOLECULAR CATALYSIS - POLYAMMONIUM MACROCYCLES AS ENZYME MIMICS FOR PHOSPHORYL TRANSFER IN ATP HYDROLYSIS [J].

HOSSEINI, MW ;

LEHN, JM ;

JONES, KC ;

PLUTE, KE ;

MERTES, KB ;

MERTES, MP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6330-6335

[19] Lewis acid catalyzed Diels-Alder reactions of highly hindered dienophiles [J].

Hubbard, RD ;

Miller, BL .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :4143-4146

[20] ROLE OF GEOMETRICAL FACTORS IN TEMPLATE EFFECTS [J].

HUC, I ;

PIETERS, RJ ;

REBEK, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :10296-10297

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