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Synlett 1999; 1999(S1): 925-929
DOI: 10.1055/s-1999-3093
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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

Jörg Velker* , Jean Philippe Roblin, Antonia Neels, Ana Tesouro, Helen Stoeckli-Evans, Frank-Gerrit Klaerner, Jan-Stefan Gehrke, Reinhard Neier
  • *Laboratoire de chimie de synthèse et de chimie biomimetique, Institut de Chimie, Av. Bellevaux 51, CH-2000 Neuchâtel, Switzerland; Fax +41(32)7 18 25 11; E-mail: Reinhard.Neier@ICH.UNINE.CH; Website: http://www.unine.ch/chim/nei1.html
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Publication Date:
31 December 1999 (online)

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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 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.

Diels-Alder reaction - Ireland-Claisen rearrangement - tandem reaction - diastereoselectivity - high pressure

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