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Regio-, Stereo- and Enantioselective α-Addition of Carbonyl Nucleophiles to Allenamides Catalyzed by a Synergistic Copper/Enamine System

preprint
revised 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

Funding

région Languedoc-Roussillon

Institut Universitaire de France IUF

Agence nationale de la recherche ANR CD2i

Centre national de la recherche scientifique

History

Email Address of Submitting Author

florian.monnier@enscm.fr

Institution

Ecole Nationale Supérieure de Chimie de Montpellier

Country

France

ORCID For Submitting Author

0000-0002-9924-2012

Declaration of Conflict of Interest

No conflict of interest