Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade.

Autor: Duchemin N; Queen Mary University of London, School of Biological and Chemical Sciences, Mile End Road, London E1 4NS, U.K., Cattoen M; Queen Mary University of London, School of Biological and Chemical Sciences, Mile End Road, London E1 4NS, U.K., Gayraud O; Queen Mary University of London, School of Biological and Chemical Sciences, Mile End Road, London E1 4NS, U.K., Anselmi S; Queen Mary University of London, School of Biological and Chemical Sciences, Mile End Road, London E1 4NS, U.K., Siddiq B; Queen Mary University of London, School of Biological and Chemical Sciences, Mile End Road, London E1 4NS, U.K., Buccafusca R; Queen Mary University of London, School of Biological and Chemical Sciences, Mile End Road, London E1 4NS, U.K., Daumas M; Sanofi Chimie, Route d'Avignon, 30390 Aramon, France., Ferey V; Sanofi R&D, 371 rue du Professeur Blayac, 34080 Montpellier, France., Smietana M; Institut des Biomolécules Max Mousseron, Université de Montpellier, CNRS, ENSCM, Place Eugène Bataillon, 34095 Montpellier, France., Arseniyadis S; Queen Mary University of London, School of Biological and Chemical Sciences, Mile End Road, London E1 4NS, U.K.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2020 Aug 07; Vol. 22 (15), pp. 5995-6000. Date of Electronic Publication: 2020 Jul 28.
DOI: 10.1021/acs.orglett.0c02079
Abstrakt: 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.
Databáze: MEDLINE