ChemInform Abstract: Sequential Heck and Diels-Alder Reactions: Facile Construction of Bicyclic Systems in a Single Synthetic Operation.
Abstract
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ChemInform Abstract
Palladium-promoted intramolecular Heck reaction of the 2-bromo-1,6- diene (I) leads to the formation of a bis(exomethylene)cyclopentane which is trapped by Diels-Alder reaction with suitable dienophiles (II) to give the bicyclic products (III). With certain dienophiles such as the acetylene (IV) and TCNE the corresponding bicyclic system (V) is obtained only in a consecutive cyclization-cycloaddition procedure. The bicyclo(4.3.0)nonenes (IIIa-c) are also prepared by cycloisomerization of the enyne (VI) in the presence of the dienophiles (IIa-c). A synthesis for the 2-bromo-1,6-diene (I) is given.
