Palladium(II) acetate mediated oxidative cyclization of ω-unsaturated α-cyano ketones for facile construction of methylenecyclohexane ring system

Palladium(II) acetate mediated oxidative cyclization of ω-unsaturated α-cyano ketones for facile construction of methylenecyclohexane ring system

A highly efficient annulative approach towards the construction of the structurally attractive methylenecyclohexane ring was developed through a convenient 1,4-addition of 4-pentenylmagnesium bromide to 2-cyano-2-cycloalkenones followed by a Pd(II)-mediated oxidative cyclization of the resulting ω-u...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-06, Vol.10 (23), p.4609-4617
Hauptverfasser: Hsieh, Min-Tsang, Shia, Kak-Shan, Liu, Hsing-Jang, Kuo, Sheng-Chu
Format: Artikel
Sprache:eng
Schlagworte:
Acetates - chemistry
Cyanoketone - chemistry
Cyclization
Cyclohexanes - chemistry
Methylation
Molecular Structure
Organometallic Compounds - chemistry
Oxidation-Reduction
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Zusammenfassung:A highly efficient annulative approach towards the construction of the structurally attractive methylenecyclohexane ring was developed through a convenient 1,4-addition of 4-pentenylmagnesium bromide to 2-cyano-2-cycloalkenones followed by a Pd(II)-mediated oxidative cyclization of the resulting ω-unsaturated α-cyano ketones. Based on this newly developed protocol, polycyclic adducts bearing various ring sizes and substitutions can be prepared in moderate to high yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25161b