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

Min-Tsang Hsieh, Kak-Shan Shia, Hsing-Jang Liu, Sheng-Chu Kuo

Chinese Medicinal Research and Development Center, China Medical University Hospital, 2 Yude Road, Taichung 40447, Taiwan, ROC. d917410@alumni.nthu.edu.tw

Organic & biomolecular chemistry 2012 Jun 21

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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.

Citation

Min-Tsang Hsieh, Kak-Shan Shia, Hsing-Jang Liu, Sheng-Chu Kuo. Palladium(II) acetate mediated oxidative cyclization of ω-unsaturated α-cyano ketones for facile construction of methylenecyclohexane ring system. Organic & biomolecular chemistry. 2012 Jun 21;10(23):4609-17