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Regio-, Stereo- and Enantioselective α-Addition of Carbonyl Nucleophiles to Allenamides Catalyzed by a Synergistic Copper/Enamine System
preprintrevised on 13.04.2020, 15:23 and posted on 15.04.2020, 09:11 by Rémi Blieck, Sebastien Lemouzy, Marc Taillefer, Florian Monnier
A dual copper/enamine catalytic system is found to enable an intermolecular enantioselective α-addition of various carbonyl nucleophiles to allenamides. Secondary amine catalysts allowed the highly enantioselective addition of aldehydes, while using primary amine catalysts led to the enantioselective addition of ketoester nucleophiles. The process was found to be highly regio-, stereo- and enantio-selective and represented the first allene hydrofunctionalization using an synergistic catalysis involving copper