Issue 23, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Min-Tsang Hsieh,*a   Kak-Shan Shia,b   Hsing-Jang Liuc  and  Sheng-Chu Kuo*d  

* Corresponding authors

a Chinese Medicinal Research and Development Center, China Medical University Hospital, 2 Yude Road, Taichung 40447, Taiwan, R.O.C
E-mail: d917410@alumni.nthu.edu.tw
Tel: +886-4-22053366 ext: 5605

b Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli County 35053, Taiwan, R.O.C.

c Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, R.O.C.

d Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taiwan, R.O.C.

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.

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

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Article information

DOI
https://doi.org/10.1039/C2OB25161B
Article type
Paper
Submitted
20 Jan 2012
Accepted
10 Apr 2012
First published
10 Apr 2012

Org. Biomol. Chem., 2012,10, 4609-4617

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

M. Hsieh, K. Shia, H. Liu and S. Kuo, Org. Biomol. Chem., 2012, 10, 4609 DOI: 10.1039/C2OB25161B

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