Direct Catalytic Enantioselective Conjugate Addition of α-Substituted Benzyl Nitriles to Alkyl Acrylates

Org Lett. 2024 Mar 22;26(11):2255-2259. doi: 10.1021/acs.orglett.4c00427. Epub 2024 Mar 7.

Abstract

The first enantioselective copper-catalyzed conjugate addition of α-substituted benzyl nitriles to alkyl acrylates is described. This protocol allows the direct and 100% atom-economic generation of a nitrile-containing quaternary stereogenic center in a highly enantioselective manner. The practical application of our methodology was demonstrated through the concise formal synthesis of (-)-aphanorphine.