A palladium-catalyzed enantioselective α-allylation of deconjugated butenolides with aza-π-allylpalladium 1,4-diploes, in situ generated from palladium-mediated decarboxylation of cyclic carbamates and amide-substituted acyclic carbonates, has been successfully developed. An array of enantioenriched 2-piperidones bearing an allcarbon quaternary stereocenter were obtained in high yields with excellent enantioselectivities (up to 99% yield and 99% ee). The utility of this method was also showcased by a large-scale reaction and synthetic transformations of the product.
A copper-catalyzed decarboxylative cascade cyclization of propargylic cyclic carbonates/carbamates with pyridinium 1,4-zwitterionic thiolates is developed. A range of fused polyheterocyclic compounds are obtained in moderate to good yields with excellent diastereoselectivities. Of particular note is that four new bonds (two C−C, one C−O/N, one C−S) and four new stereocenters could be efficiently embedded into the tetracyclic fused scaffolds in a single step.
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