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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.

SUBMITTER: Stevenson SM

PROVIDER: S-EPMC5321652 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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C-C Bond Migration in the Cycloisomerization of 1,6-Enynes.

Stevenson Susan M SM Newcomb Eric T ET Ferreira Eric M EM

Organic chemistry frontiers : an international journal of organic chemistry 20160630 10

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. ...[more]

PMID: 28239480

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