Recognition-induced control of a Diels-Alder cycloaddition

Andrew Robertson; Douglas Philp; Neil Spencer

doi:10.1016/S0040-4020(99)00633-X

Recognition-induced control of a Diels-Alder cycloaddition

Andrew Robertson, Douglas Philp^*, Neil Spencer

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	11365-11384
Number of pages	20
Journal	Tetrahedron
Volume	55
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4020(99)00633-X
State	Published - Sep 10 1999

Keywords

Cycloaddition
Furans
Kinetics
Molecular recognition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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AU - Philp, Douglas

AU - Spencer, Neil

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N2 - 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.

AB - 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.

KW - Cycloaddition

KW - Furans

KW - Kinetics

KW - Molecular recognition

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EP - 11384

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 37

ER -

Recognition-induced control of a Diels-Alder cycloaddition

Abstract

Keywords

ASJC Scopus subject areas

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