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

doi:10.1055/s-1999-3093

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

Author(s)

Velker, Jörg

Roblin, Jean-Philippe

Neels, Antonia

Tesouro, Ana

Stoeckli-Evans, Helen

Institut de chimie

Klaerner, Frank-Gerrit

Gehrke, Jan-Stefan

Neier, Reinhard

Institut de chimie

Date issued

1999

In

Synlett, Georg Thieme, 1999/1//925-929

Subjects

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

Abstract

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.