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  • 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.

Organic & biomolecular chemistry (2012-05-15)
Min-Tsang Hsieh, Kak-Shan Shia, Hsing-Jang Liu, Sheng-Chu Kuo
ABSTRACT

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.

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Sigma-Aldrich
Methylenecyclohexane, 98%