Recognition-mediated facilitation of a disfavored Diels-Alder reaction

Authors
Bennes, R Philp, D Spencer, N Kariuki, BM Harris, KDM
Citation
R. Bennes et al., Recognition-mediated facilitation of a disfavored Diels-Alder reaction, ORG LETT, 1(7), 1999, pp. 1087-1090
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
7
Year of publication
1999
Pages
1087 - 1090
Database
ISI
SICI code
1523-7060(19991007)1:7<1087:RFOADD>2.0.ZU;2-6
Abstract
[GRAPHICS] The rational design of a system which is capable of accelerating and facili tating a thermodynamically disfavored Diets-Alder cycloaddition between a f uran and a maleimide is presented. The origins of the acceleration and faci litation of the cycloaddition reaction are traced by kinetic studies-allied to results from H-1 NMR spectroscopy and X-ray crystallography-to the form ation of strong intramolecular hydrogen bonds in the cycloadduct.