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Issue 1, 2017
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Dearomatisation approaches to spirocyclic dienones via the electrophilic activation of alkynes

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Abstract

Two complementary dearomatising spirocyclisation protocols to generate spirocyclic dienones from anisole and phenol-tethered ynones are described, each proceeding via electrophilic alkyne activation. The first approach focuses on the spirocyclisation of para-substituted anisoles using either SnCl2·2H2O or Cu(OTf)2. The second approach, which enables the spirocyclisation of both ortho- and para-substituted phenols, uses silica-supported AgNO3 to generate similar scaffolds with much greater efficiency. Initial asymmetric studies are also outlined.

Graphical abstract: Dearomatisation approaches to spirocyclic dienones via the electrophilic activation of alkynes

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Article information


Submitted
07 Nov 2016
Accepted
22 Nov 2016
First published
23 Nov 2016

Org. Biomol. Chem., 2017,15, 233-245
Article type
Paper

Dearomatisation approaches to spirocyclic dienones via the electrophilic activation of alkynes

A. K. Clarke, J. T. R. Liddon, J. D. Cuthbertson, R. J. K. Taylor and W. P. Unsworth, Org. Biomol. Chem., 2017, 15, 233
DOI: 10.1039/C6OB02426B

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