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The High Stereoselectivity of the Tandem Sequence Diels-Alder Reaction/Ireland-Claisen Rearrangement Starting from Substituted O-(<i>E</i>)-Buta-1,3-dienyl Ketene Acetals and Cyclic Dienophiles
Auteur(s)
Soldermann, Nicolas
Velker, Jörg
Neels, Antonia
Date de parution
2007
In
Synthesis, Georg Thieme, 2007/15//2379-2387
Résumé
A new tandem reaction leads to bicyclic cyclohexene derivatives with complete control of the relative configuration of the four chiral centers formed. The high diastereoselectivity is the consequence of an endo-selective Diels-Alder reaction followed by an Ireland-Claisen rearrangement that proceeds via a boat-like transition state.
Identifiants
Type de publication
journal article
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