A completely selective and strongly accelerated Diels-Alder reaction mediated by hydrogen bonding

Russell J. Pearson; Eleftherios Kassianidis; Douglas Philp

doi:10.1016/j.tetlet.2004.04.079

A completely selective and strongly accelerated Diels-Alder reaction mediated by hydrogen bonding

Russell J. Pearson, Eleftherios Kassianidis, Douglas Philp^*

^*Corresponding author for this work

Chemistry

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

27 Scopus citations

Abstract

A Diels-Alder cycloaddition between a furan and a maleimide is presented in which the presence of complementary hydrogen bonding sites dramatically accelerate the reaction and, additionally, ensure that only one of two possible diastereoisomers is formed.

Original language	English (US)
Pages (from-to)	4777-4780
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.079
State	Published - Jun 7 2004

Keywords

Cycloaddition
Diels-Alder
Hydrogen-bonding
Molecular recognition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.04.079

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title = "A completely selective and strongly accelerated Diels-Alder reaction mediated by hydrogen bonding",

abstract = "A Diels-Alder cycloaddition between a furan and a maleimide is presented in which the presence of complementary hydrogen bonding sites dramatically accelerate the reaction and, additionally, ensure that only one of two possible diastereoisomers is formed.",

keywords = "Cycloaddition, Diels-Alder, Hydrogen-bonding, Molecular recognition",

author = "Pearson, {Russell J.} and Eleftherios Kassianidis and Douglas Philp",

note = "Funding Information: This work was supported by the BBSRC (Grant B11855), the EPSRC (DTA award to E.K.) and the University of St Andrews. We thank Professor G. von Kiedrowski for providing us with a copy of his SimFit program and Melanja Smith for technical assistance. ",

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doi = "10.1016/j.tetlet.2004.04.079",

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T1 - A completely selective and strongly accelerated Diels-Alder reaction mediated by hydrogen bonding

AU - Pearson, Russell J.

AU - Kassianidis, Eleftherios

AU - Philp, Douglas

N1 - Funding Information: This work was supported by the BBSRC (Grant B11855), the EPSRC (DTA award to E.K.) and the University of St Andrews. We thank Professor G. von Kiedrowski for providing us with a copy of his SimFit program and Melanja Smith for technical assistance.

PY - 2004/6/7

Y1 - 2004/6/7

N2 - A Diels-Alder cycloaddition between a furan and a maleimide is presented in which the presence of complementary hydrogen bonding sites dramatically accelerate the reaction and, additionally, ensure that only one of two possible diastereoisomers is formed.

AB - A Diels-Alder cycloaddition between a furan and a maleimide is presented in which the presence of complementary hydrogen bonding sites dramatically accelerate the reaction and, additionally, ensure that only one of two possible diastereoisomers is formed.

KW - Cycloaddition

KW - Diels-Alder

KW - Hydrogen-bonding

KW - Molecular recognition

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DO - 10.1016/j.tetlet.2004.04.079

M3 - Article

AN - SCOPUS:2442639984

SN - 0040-4039

VL - 45

SP - 4777

EP - 4780

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

A completely selective and strongly accelerated Diels-Alder reaction mediated by hydrogen bonding

Abstract

Keywords

ASJC Scopus subject areas

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