Filling the Gaps in the Challenging Asymmetric Hydrogenation of Exocyclic Benzofused Alkenes with Ir-P

Identifier:  imarina:9283365

Handle: https://hdl.handle.net/20.500.11797/imarina9283365

Authors:  Biosca, Maria; de la Cruz-Sanchez, Pol; Tarr, Daniel; Llanes, Patricia; Karlsson, Erik A; Margalef, Jessica; Pamies, Oscar; Pericas, Miquel A; Dieguez, Montserrat

Abstract:
Herein, we report a chiral phosphine-triazole ligand for the Ir-catalyzed asymmetric hydrogenation of exocyclic benzofused alkenes. Overcoming previous limitations, the catalytic system is able to successfully hydrogenate exocyclic olefins bearing a benzofused five- and six-membered ring motif (ee's between 92 to 99%). The catalyst tolerates well the presence of several substituents and substitution patterns at both aromatic rings. The absence of a competing isomerization process together with the perfect fit of the olefins in the catalyst chiral pocket are key to surpass the previous limitations in the hydrogenation of both 5- and 6-membered ring benzofused exocyclic olefins.