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

• DOI: 10.1021/ol503121q
• Publication Date: 2014-11-19T15:40:29Z
• Authors: Paloma Bernal-Albert; Hélio Faustino; Ana Gimeno; Gregorio Asensio; José L. Mascareñas; Fernando López
• Keywords: 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

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.