Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes

Cycloaddition Reaction Molecular Structure Hydrazones Materias::Investigación::23 Química Stereoisomerism Allenamides 01 natural sciences Catalysis 0104 chemical sciences :Investigación::23 Química [Materias] Alkadienes Combinatorial Chemistry Techniques Gold Cycloaddition Cyclobutanes
DOI: 10.1021/ol503121q Publication Date: 2014-11-19T15:40:29Z
ABSTRACT
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.
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