ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

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

preprint
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.

History

Email Address of Submitting Author

s.arseniyadis@qmul.ac.uk

Institution

Queen Mary University of London

Country

United Kingdom

ORCID For Submitting Author

0000-0001-6831-2631

Declaration of Conflict of Interest

The authors declare no competing financial interest.

Exports