Palladium-catalyzed sequential reaction viaSonogashira coupling, isomerization, Claisen rearrangement and [4 + 2] cycloaddition sequence for the rapid synthesis of tricyclo[3.2.1.02,7]oct-3-ene derivatives

Shugao Zhu; Luling Wu; Xian Huang

doi:10.1039/C1RA00452B

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Palladium-catalyzed sequential reaction viaSonogashira coupling, isomerization, Claisen rearrangement and [4 + 2] cycloaddition sequence for the rapid synthesis of tricyclo[3.2.1.0^2,7]oct-3-ene derivatives†

Shugao Zhu,^a Luling Wu*^a and Xian Huang ‡^ab

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* Corresponding authors

^a Department of Chemistry, Zhejiang University, Hangzhou, P. R. China

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China
E-mail: Wululing@zju.edu.cn

Abstract

An interesting sequential reaction consisting of Sonogashira coupling, propargyl–allenyl isomerization, allenyl–benzyl Claisen rearrangement and [4 + 2] cycloaddition was developed. This reaction provides an efficient synthesis of fused tricyclo[3.2.1.0^2,7]oct-3-enes.

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Article information

DOI: https://doi.org/10.1039/C1RA00452B
Article type: Communication
Submitted: 14 Jul 2011
Accepted: 03 Oct 2011
First published: 03 Nov 2011

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RSC Adv., 2012,2, 132-134

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Palladium-catalyzed sequential reaction viaSonogashira coupling, isomerization, Claisen rearrangement and [4 + 2] cycloaddition sequence for the rapid synthesis of tricyclo[3.2.1.0^2,7]oct-3-ene derivatives

S. Zhu, L. Wu and X. Huang, RSC Adv., 2012, 2, 132 DOI: 10.1039/C1RA00452B

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