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endo- and exo-Stereochemistry in the Diels-Alder Reaction: Kinetic versus Thermodynamic Control
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Abstract
In these experiments, which were used in the problem-solving mode, the stereoselectivity of the Diels-Alder cycloaddition of N-phenylmaleimide to furan is deduced by the characteristic splitting patterns in the proton-NMR spectra. The relationship of coupling constants to dihedral angle, as described by the Karplus equation, is illustrated. The data can also be used to demonstrate the concept of kinetic versus thermodynamic control.
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This article has been cited by 11 ACS Journal articles (5 most recent appear below).
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- Received: August 03, 2009
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