Application of P,N-sulfinyl imine ligands to iridium-catalyzed asymmetric hydrogenation of olefins.
The utility of a novel class of P,N-ligands incorporating a chiral sulfinyl imine moiety is demonstrated in the iridium-catalyzed hydrogenation of both functionalized and unfunctionalized olefins, in which enantioselectivities of up to 94% are achieved. The modularity of the P,N-sulfinyl ligand class is highlighted by the facile preparation of a variety of sterically and electronically different ligands. Interesting structure-activity data for both the phosphine and sulfinamide components is provided by this expanded ligand set.
Schenkel
Laurie B
LB
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Ellman
Jonathan A
JA
D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D007097:Imines / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D008024:Ligands; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry; D013452:Sulfonium Compounds / Q000737:chemistry*
D000475:Alkenes; D000577:Amides; D007097:Imines; D008024:Ligands; D010720:Phosphines; D013267:Stilbenes; D013452:Sulfonium Compounds; D007495:Iridium