Issue 40, 2014
From the journal:

Chemical Communications

Palladium-catalyzed cyclization of bromoenynamides to tricyclic azacycles: synthesis of trikentrin-like frameworks†

Craig D. Campbell,a   Rebecca L. Greenaway,a   Oliver T. Holton,a   Helen A. Chapmanb  and  Edward A. Anderson*a  

* Corresponding authors

a Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK
E-mail: edward.anderson@chem.ox.ac.uk
Fax: +44 (0)1865 285002
Tel: +44 (0)1865 285000

b Syngenta Ltd., Jealott's Hill International Research Centre, Bracknell, Berkshire, UK

Abstract

Palladium-catalyzed cascade cyclization of bromoenynamides equipped with an additional alkyne or ynamide substituent affords azatricyclic products. Using 5- to 7-membered ring tethers, this chemistry offers a regiospecific route to highly-functionalized azacycles. Elaboration to the trikentrin B skeleton is achieved from the arylsilane cyclization products.

Graphical abstract: Palladium-catalyzed cyclization of bromoenynamides to tricyclic azacycles: synthesis of trikentrin-like frameworks

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Article information

DOI
https://doi.org/10.1039/C3CC45634J
Article type
Communication
Submitted
24 Jul 2013
Accepted
15 Aug 2013
First published
22 Aug 2013
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 5187-5189

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Palladium-catalyzed cyclization of bromoenynamides to tricyclic azacycles: synthesis of trikentrin-like frameworks

C. D. Campbell, R. L. Greenaway, O. T. Holton, H. A. Chapman and E. A. Anderson, Chem. Commun., 2014, 50, 5187 DOI: 10.1039/C3CC45634J

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