Synthesis of 2-(1,4-dioxaspiro[4,5]decan-6-yl)acrylamides from 2-acetylcyclohexanone via palladium-catalysed aminocarbonylation

Farkas, Roland and Petz, Andrea and Kollár, László (2015) Synthesis of 2-(1,4-dioxaspiro[4,5]decan-6-yl)acrylamides from 2-acetylcyclohexanone via palladium-catalysed aminocarbonylation. MONATSHEFTE FÜR CHEMIE, 146 (10). pp. 1665-1671. ISSN 0026-9247

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Abstract

6-(1-Iodovinyl)-1,4-dioxaspiro[4.5]decane, an iodoalkene obtained from 2-acetylcyclohexanone via ethylene ketal formation, hydrazone formation and iodination, was aminocarbonylated in the presence of a palladiumphosphine precatalyst. Systematic investigations revealed that 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides can be obtained in high yields via palladium-catalysed aminocarbonylation. The influence of the amine nucleophiles and of the reaction conditions on the isolated yields was investigated.

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