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Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a Formal Cross Rauhut-Currier Reaction

submitted on 24.04.2020, 00:29 and posted on 28.04.2020, 07:23 by Nicolas Duchemin, Martin Cattoen, Oscar Gayraud, Silvia Anselmi, Bilal Siddiq, Roberto Buccafusca, Marc Daumas, Vincent Ferey, Michael Smietana, Stellios Arseniyadis
A highly enantioselective synthesis of α-branched acrylonitriles is reported featuring an unprecedented formal cross Rauhut-Currier reaction consisting of an asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which involves the use of an acrylonitrile surrogate, is practical, scalable and highly versatile, and provides a straightforward access to a wide range of enantioenriched nitrile-containing building blocks without using acrylonitrile or any source of cyanide. Most importantly, it offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.


Email Address of Submitting Author


Queen Mary University of London


United Kingdom

ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no competing financial interest.