BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome?
In discovering the remarkable catalytic properties of BINOL-derived phosphoramidites (binoP-NR(2)), Dutch researchers recently achieved a long-awaited breakthrough in asymmetric catalysis. For the first time, easily accessible monodentate chiral P(III) ligands turned out to provide high enantioselectivities when used in rhodium-catalysed olefin hydrogenation. The simplest ligand representative of this family is MonoPhos, which can be made straightforwardly from BINOL and hexamethylphosphorous triamide. Since the first publication dealing with such catalysts (J. Am. Chem. Soc., 2000), a variety of binoP-NRR' ligands have been reported in which the amino group bears a functional substituent or a stereogenic centre. This critical review examines the impact of the presence of such a functionality in the amino group on catalytic olefin hydrogenation reactions.
Eberhardt
Luc
L
Laboratoire de Chimie Inorganique Moléculaire, Institut de Chimie, UMR 7177 CNRS-Université Louis Pasteur, 1 rue Blaise Pascal, F-67008, Strasbourg Cedex, France.
Armspach
Dominique
D
Harrowfield
Jack
J
Matt
Dominique
D
D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000588:Amines; C406944:BINOL, naphthol; D009284:Naphthols; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D012238:Rhodium