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Issue 10, 2016
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C–C bond migration in the cycloisomerization of 1,6-enynes

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Abstract

A full account of our investigation of C–C bond migration in the cycloisomerization of oxygen-tethered 1,6-enynes is described. Under Pt(II) and/or Ir(I) catalysis, cyclic and acylic alkyl groups were found to undergo 1,2-shifts into metal carbenoid intermediates. Interestingly, this process does not appear to be driven by the release of ring strain, and thus provides access to large carbocyclic frameworks. The beneficial effect of CO on the Pt(II) and Ir(I) catalytic systems is also evaluated.

Graphical abstract: C–C bond migration in the cycloisomerization of 1,6-enynes

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Supplementary files

Article information


Submitted
26 May 2016
Accepted
30 Jun 2016
First published
30 Jun 2016

Org. Chem. Front., 2016,3, 1228-1235
Article type
Research Article
Author version available

C–C bond migration in the cycloisomerization of 1,6-enynes

S. M. Stevenson, E. T. Newcomb and E. M. Ferreira, Org. Chem. Front., 2016, 3, 1228 DOI: 10.1039/C6QO00224B

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