Synthesis of 1,5-methano-3-benzazocines by intramolecular Buchwald–Hartwig arylation of 2-piperidinones

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• 作者：Gedu Satyanarayana ; Martin E. Maier
• 关键词：Cyclization ; Pd catalysis ; Arylation ; Benzazocines ; Scaffolds
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：7 January 2008
• 年：2008
• 卷：64
• 期：2
• 页码：356-363
• 全文大小：330 K

文摘

A conceptually novel route to 1,5-methano-3-benzazocines based on an intramolecular Buchwald–Hartwig arylation was developed. The reaction required the use of the zinc enolate of the piperidinone substrates. These substrates, piperidin-2-ones with a 2-bromobenzyl substituent in the 5-position were prepared by reductive amination of 4-formyl esters. The latter could be obtained via Michael addition of enamines, derived from 3-arylpropanals, to ethyl acrylate.