Filling the Gaps in the Challenging Asymmetric Hydrogenation of Exocyclic Benzofused Alkenes with Ir−P, N Catalysts. Issue 2 (11th October 2022)

• Record Type: Journal Article
• Authors: Biosca, Maria; de la Cruz‐Sánchez, Pol; Tarr, Daniel; Llanes, Patricia; Karlsson, Erik A.; Margalef, Jèssica; Pàmies, Oscar; Pericàs, Miquel A.; Diéguez, Montserrat
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 2(2023)
• Page Start: 167
• Page End: 177
• Publication Date: 2022-10-11
• Subjects: Exocyclic olefins -- asymmetric hydrogenation -- iridium -- P, N-ligands -- deuterogenation -- DFT calculations; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200870
• Languages: English
• ISSNs: 1615-4150

Abstract

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. Abstract :