Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade
Nicolas Duchemin, Martin Cattoen, Oscar Gayraud, Silvia Anselmi, Bilal Siddiq, Roberto Buccafusca, Marc Daumas, Vincent Ferey, Michaël Smietana, Stellios Arseniyadis
Abstract
A highly enantioselective synthesis of α-branched acrylonitriles is reported featuring a one-pot sequential asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which relies on a solid, bench-stable, and commercially available acrylonitrile surrogate, is practical, scalable, and highly versatile and provides a direct access to a wide range of enantioenriched nitrile-containing building blocks. Most importantly, the method offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.
Topics & Concepts
Michael reactionAcrylonitrileMoietyCascadeChemistryEnantioselective synthesisNitrileCombinatorial chemistryStereochemistryOrganic chemistryPolymerCopolymerCatalysisChromatographyAsymmetric Hydrogenation and CatalysisChemical Synthesis and ReactionsAsymmetric Synthesis and Catalysis