The novel sequence Diels-Alder reaction/Ireland-Claisen rearrangement applied to acyclic dienophiles: New insights into the selectivity of the Ireland-Claisen rearrangement

Authors
Velker, J Roblin, JP Neels, A Tesouro, A Stoeckli-Evans, H Klaerner, FG Gehrke, JS Neier, R
Citation
J. Velker et al., The novel sequence Diels-Alder reaction/Ireland-Claisen rearrangement applied to acyclic dienophiles: New insights into the selectivity of the Ireland-Claisen rearrangement, SYNLETT, 1999, pp. 925-929
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Year of publication
1999
Pages
925 - 929
Database
ISI
SICI code
0936-5214(1999):<925:TNSDRR>2.0.ZU;2-9
Abstract
The new dienes 4a-d, 7 and 11 reacted in good yields with acyclic dienophil es like methyl acrylate and diethyl fumarate in the tandem process Diels-Al der reaction/Ireland-Claisen rearrangement. Analysis of the relative config uration of products 5, 6, 8-10 and 12 indicated that preference for the cha ir or boat transition state of the Ireland-Claisen rearrangement is strongl y influenced by the relative configuration of the substituents of the cyclo hexene ring.