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Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes.

ABSTRACT: Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,5-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.

SUBMITTER: Felix RJ

PROVIDER: S-EPMC3788353 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes.

Felix Ryan J RJ Gutierrez Osvaldo O Tantillo Dean J DJ Gagné Michel R MR

The Journal of organic chemistry 20130513 11

Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,5-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transfo ...[more]

PMID: 23663099

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