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

38 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

Access to Document

10.1016/S0040-4020(99)00633-X

Cite this

@article{56c8c25a571e4d0db34de9cc406f2bd6,

title = "Recognition-induced control of a Diels-Alder cycloaddition",

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.",

keywords = "Cycloaddition, Furans, Kinetics, Molecular recognition",

author = "Andrew Robertson and Douglas Philp and Neil Spencer",

note = "Funding Information: This research was supported by the University of Birmingham, the Engineering and Physical Sciences Research Council (Quota Award to A.R.), and the Biotechnology and Biological Sciences Research Council (Grants 6/B03840 and 6/B04100). We thank Prof G. yon Kiedrowski for supplying us with a copy of his SimFit program.",

year = "1999",

month = sep,

day = "10",

doi = "10.1016/S0040-4020(99)00633-X",

language = "English (US)",

volume = "55",

pages = "11365--11384",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "37",

}

TY - JOUR

T1 - Recognition-induced control of a Diels-Alder cycloaddition

AU - Robertson, Andrew

AU - Philp, Douglas

AU - Spencer, Neil

N1 - Funding Information: This research was supported by the University of Birmingham, the Engineering and Physical Sciences Research Council (Quota Award to A.R.), and the Biotechnology and Biological Sciences Research Council (Grants 6/B03840 and 6/B04100). We thank Prof G. yon Kiedrowski for supplying us with a copy of his SimFit program.

PY - 1999/9/10

Y1 - 1999/9/10

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

UR - http://www.scopus.com/inward/record.url?scp=0033543474&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033543474&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(99)00633-X

DO - 10.1016/S0040-4020(99)00633-X

M3 - Article

AN - SCOPUS:0033543474

VL - 55

SP - 11365

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

Access to Document

Other files and links

Fingerprint

Cite this