Faculté des sciences

The Novel Sequence Diels-Alder Reaction/Ireland-Claisen Rearrangement Applied to Acyclic Dienophiles: New Insights into the Selectivity of the Ireland-Claisen Rearrangement

Velker, Jörg ; Roblin, Jean-Philippe ; Neels, Antonia ; Tesouro, Ana ; Stoeckli-Evans, Helen ; Klaerner, Frank-Gerrit ; Gehrke, Jan-Stefan ; Neier, Reinhard

In: Synlett, 1999, vol. 1, p. 925-929

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 rearangement. 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... Plus

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    Summary
    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 rearangement. 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 stronlgy influenced by the relative configuration of the substituents of the cyclohexene ring.