Chiral pyranoside phosphite-oxazolines: a new class of ligand for asymmetric catalytic hydrogenation of alkenes.
We have described the first successful application of a phosphite-oxazoline ligand library in the asymmetric Ir-catalyzed hydrogenation of several unfunctionalized olefins. The introduction of a bulky biaryl phosphite moiety in the ligand design is highly adventitious in the product outcome. By carefully selecting the ligand components, we obtained high activities (TOFs up to >1500 mol x (mol x h)(-1) at 1 bar of H2) and enantioselectivities (ee values up to >99%) and, at the same time, show a broad scope for different substrate types. So, this is an exceptional ligand class that competes favorably with a few other ligand series that also provide high ee values for tri- and disubstituted substrate types.
Diéguez
Montserrat
M
Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, C/ Marcel.lí Domingo, s/n 43007 Tarragona, Spain.
Mazuela
Javier
J
Pàmies
Oscar
O
Verendel
J Johan
JJ
Andersson
Pher G
PG
D000473:Alkanes / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry; D008024:Ligands; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D017905:Phosphites / Q000138:chemical synthesis / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000473:Alkanes; D000475:Alkenes; D008024:Ligands; D010080:Oxazoles; D017905:Phosphites; D011714:Pyrans; C064210:oxazolidine; D007495:Iridium