RESUMEN
The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N3-, followed by a subsequent CuAAC reaction with arylacetylenes to install a 1,4-triazolo moiety. The approach allows for modification to both the sulfoxonium ylide and arylacetylene reactants. Fifteen examples have been reported, with yields ranging between 22% and 75%.
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CetonasRESUMEN
A synthetic method to prepare partially hydrogenated isoquinolines efficiently from silver-mediated [3,3]-sigmatropic rearrangement/Diels-Alder reaction of 1,9-dien-4-yne esters is described. The reactions were shown to be robust with a wide variety of substitution patterns tolerated to provide the corresponding nitrogen-containing heterocyclic products in good to excellent yields. This includes examples containing a bridgehead sp3 quaternary carbon center as well as the cycloisomerization of one substrate to give the corresponding bicyclic adduct in excellent yield at the gram scale.
RESUMEN
A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Brønsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.
