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, Joerg
Roblin, Jean Philippe
Neels, Antonia
Tesouro, Ana
Klaerner, Frank-Gerrit
Gehrke, Jan-Stefan
Date issued
January 12, 1999
In
Synlett
From page
925
To page
929
Subjects
Dials-Alder reaction Ireland-Claisen rearrangement tandem reaction diastereoselectivity high pressure ORGANIC-SYNTHESIS ACRYLOYL CHLORIDE TANDEM REACTIONS ALKALOIDS ACETALS SHIFT ESTER ACID
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 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.
Publication type
journal article