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Gold(I)-catalyzed intermolecular cycloaddition of allenamides with ?,?-unsaturated hydrazones: efficient access to highly substituted cyclobutanes.

ABSTRACT: ?,?-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.

SUBMITTER: Bernal-Albert P

PROVIDER: S-EPMC4304836 | biostudies-other | 2014 Dec

REPOSITORIES: biostudies-other

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Gold(I)-catalyzed intermolecular cycloaddition of allenamides with α,β-unsaturated hydrazones: efficient access to highly substituted cyclobutanes.

Bernal-Albert Paloma P Faustino Hélio H Gimeno Ana A Asensio Gregorio G Mascareñas José L JL López Fernando F

Organic letters 20141119 23

α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields. ...[more]

PMID: 25406491

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