146558-42-1Relevant articles and documents
Extending the substrate scope of bicyclic p-oxazoline/thiazole ligands for ir-catalyzed hydrogenation of unfunctionalized olefins by introducing a biaryl phosphoroamidite group
Biosca, Maria,Paptchikhine, Alexander,P??mies, Oscar,Andersson, Pher G.,Di??guez, Montserrat
, p. 3455 - 3464 (2015/03/04)
This study identifies a series of Ir-bicyclic phosphoroamidite-oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E- and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and ?±,?2-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite-oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane-oxazoline/thiazole ligands, by replacing the N-phosphane group with a p-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite-oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the Ndonor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N-phosphane-oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.
