Issue 17, 2000
From the journal:

Chemical Communications

Diels–Alder chemistry of 2-cyanoalk-2-enones. A convenient general approach to angularly substituted polycyclic systems

Jia-Liang Zhu,a   Kak-Shan Shiab  and  Hsing-Jang Liu*a  

* Corresponding authors

a Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada

b Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, Republic of China.
E-mail: hjliu@mx.nthu.edu.tw

Abstract

Under zinc chloride catalysis, a number of 2-cyanoalk-2-enones representing various ring sizes were found to undergo facile cycloaddition with several selected conjugated dienes; sequential treatment of the adducts with lithium naphthalenide and an alkylating agent resulted in the direct replacement of the angular cyano group with an alkyl group, providing easy access to angularly substituted polycyclic systems.

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Article information

DOI
https://doi.org/10.1039/B004297H
Article type
Communication
Submitted
31 May 2000
Accepted
30 Jun 2000
First published
04 Aug 2000

Chem. Commun., 2000, 1599-1600

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Diels–Alder chemistry of 2-cyanoalk-2-enones. A convenient general approach to angularly substituted polycyclic systems

J. Zhu, K. Shia and H. Liu, Chem. Commun., 2000, 1599 DOI: 10.1039/B004297H

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