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Benzoazabicyclo[4.3.1] derivatives by intramolecular Michael addition of piperidinone enolates to enoates

✍ Scribed by Gedu Satyanarayana; Sven Müller; Martin E. Maier

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
187 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

Piperidinones with a 2-bromobenzyl substituent in the 5-position were subjected to a Heck coupling reaction with ethyl acrylate resulting in the highly functionalized cinnamates 9a-d. A subsequent deprotonation of the piperidinones using NaN(SiM 3 ) 2 in THF induced an intramolecular Michael addition of the enolate to the cinnamate part. In this way, a range of novel 2,6-methano-4H-4-benzazonines 10-13 were obtained. In each case, a separable mixture of endo/exo-diastereomers was obtained.

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