6533b870fe1ef96bd12d0378

RESEARCH PRODUCT

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

Paloma Bernal-albertJosé L. MascareñasAna GimenoHélio FaustinoFernando Toboso LópezFernando Toboso LópezFernando Toboso LópezGregorio Asensio

subject

chemistry.chemical_classificationCyclobutaneschemistryIntermolecular forceHydrazoneMoietyGeneral MedicineMedicinal chemistryCycloadditionCatalysis

description

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.

https://doi.org/10.1002/chin.201520075