The novel sequence Diels-Alder reaction/Ireland-Claisen rearrangement applied to acyclic dienophiles: New insights into the selectivity of the Ireland-Claisen rearrangement
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The new dienes 4a-d, 7 and 11 reacted in good yields with acyclic dienophiles like methyl acrylate and diethyl fumarate in the tandem process Diels-Alder reaction/Ireland-Claisen rearrangement. Analysis of the relative configuration of products 5, 6, 8-10 and 12 indicated that preference for the chair or boat transition state of the Ireland-Claisen rearrangement is strongly influenced by the relative configuration of the substituents of the cyclohexene ring.
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