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

Bernal Albert, PalomaFaustino, HélioGimeno, AnaAsensio, GregorioMascareñas Cid, José LuisLópez García, Fernando2015-02-202015-02-202014-11-19Bernal-Albert, P., Faustino, H., Gimeno, A., Asensio, G., Mascareñas, J.L. and López, F. (2014). Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes. Org. Lett., 2014,16 (23), pp. 6196–6199. doi: 10.1021/ol503121q1523-7060E-ISSN 1523-7052http://hdl.handle.net/10347/12379α,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 yieldseng© American Chemical SocietyGoldCatalysisCycloadditionAllenamidesCyclobutanesHydrazonesMaterias::Investigación::23 QuímicaGold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanesjournal article10.1021/ol503121qopen access