Issue 10, 2016

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
26 میٔ 2016
Accepted
30 جوٗن 2016
First published
30 جوٗن 2016

Org. Chem. Front., 2016,3, 1228-1235

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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