Science and Technology Production
Article
Authorship
Date
2006
Publishing House and Editing Place
Wiley-VCH Verlag GmbH & Co. KGaA
Magazine
ADVANCED SYNTHESIS & CATALYSIS (PRINT)
(pp. 463-470)
Wiley-VCH Verlag GmbH & Co. KGaA
Summary
Information provided by the agent in
SIGEVA
The title compounds were prepared by a facile [4+3]-cycloaddition strategy involving sonochemistry. The oxyallyl species required for the reaction with the corresponding diene was generated from a suitable perbromo ketone with activated zinc under sonification conditions. The resulting dibromo bicyclo compounds were reduced to the target products using a Cu/Zn couple. Ring-opening cross metathesis of the resulting bicyclic species was established as an efficient method for the diastereoselectiv...
The title compounds were prepared by a facile [4+3]-cycloaddition strategy involving sonochemistry. The oxyallyl species required for the reaction with the corresponding diene was generated from a suitable perbromo ketone with activated zinc under sonification conditions. The resulting dibromo bicyclo compounds were reduced to the target products using a Cu/Zn couple. Ring-opening cross metathesis of the resulting bicyclic species was established as an efficient method for the diastereoselective preparation of >-3,5-disubstituted cycloketones. Especially gaseous olefins gave symmetrical and unsymmetrical products as versatile platforms for subsequent transformations. This is the first example of such a ringopening reaction of a non-strained ring system.
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Key Words
RING-OPENING CROSS METATHESISGRUBBS CATALYSTGASEOUS ALKENESSONOCHEMISTRY[4+3]-CYCLOADDITIONRUTHENIUM