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Diastereoselective synthesis of bicyclo[2.2.2]octanes by double Michael addition

✍ Scribed by Dietrich Spitzner; Peter Wagner; Arndt Simon; Karl Peters

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
203 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Several chiral acrylates (7b-f) react with kinetically controlled generated lithium dienolate 6a to form chiral bicyclot2.2.2loctanes 4 with modest d.e.. It was found, that the diastereoselection is improved, when the corrssponding trimethylsilyl ether 6b reacts with chiral acrylates under Lewis acid catalysis. The absolute stereochemistry of these bicycloI2.2.2loctanes was determined by X-ray analysis.

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