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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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methylenecyclohexane, 98%