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The Novel Sequence Diels-Alder Reaction/Ireland-Claisen Rearrangement Applied to Acyclic Dienophiles: New Insights into the Selectivity of the Ireland-Claisen Rearrangement
Auteur(s)
Velker, Jörg
Roblin, Jean-Philippe
Neels, Antonia
Tesouro, Ana
Klaerner, Frank-Gerrit
Gehrke, Jan-Stefan
Date de parution
1999
In
Synlett, Georg Thieme, 1999/1//925-929
Résumé
The new dienes <b>4a-d, 7</b> and <b>11</b> 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 <b>5, 6, 8-10</b> and <b>12</b> 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.
Identifiants
Type de publication
journal article
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