Enantioselective Addition of Alkynyl Ketones to Nitroolefins Assisted by Bronsted Base/H-Bonding Catalysis
Ikusi/ Ireki
Data
2019-03-21Egilea
Campano García, Teresa Esperanza
Iriarte Arrieta, Igor
Olaizola Aizpuru, Olatz
Etxabe Tellería, Julen
Gamboa Landa, José Ignacio
Odriozola, José M.
García, Jesús María
Palomo Nicolau, Claudio
Chemistry 25(17) : 4390-4397 (2019)
Laburpena
Various sets of enolizable alkynyl ketones (including methyl ynones with α-aryl, α-alkenyl, and α-alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H-bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo- and enantioselective fashion. Further transformation of the obtained adducts into optically active acyclic and polycyclic molecules, including some with intricate carbon skeletons, was also demonstrated.