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Recognition-Mediated Facilitation of a Disfavored Diels−Alder Reaction

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posted on 04.09.1999, 00:00 by Raphaël Bennes, Douglas Philp, Neil Spencer, Benson M. Kariuki, Kenneth D. M. Harris
The rational design of a system which is capable of accelerating and facilitating a thermodynamically disfavored Diels−Alder cycloaddition between a furan and a maleimide is presented. The origins of the acceleration and facilitation of the cycloaddition reaction are traced by kinetic studiesallied to results from 1H NMR spectroscopy and X-ray crystallographyto the formation of strong intramolecular hydrogen bonds in the cycloadduct.