(R)-1-{(S)-2-[DI(1-NAPHTHYL)PHOSPHINO]FERROCENYL}ETHYLDI(3,5-XYLYL)PHOSPHINE

Reactions

1. Ferrocenylphosphine ligands of the type cpFecp(PR2)(*CH(CH3)PR'2) are a class of asymmetric ligands developed at Solvias in Basel, Switzerland. Ligands of this type are currently used industrially in the stereoselective synthesis of commercial products. A unique feature of these bidentate ligands is the presence of a fixed phosphine moiety and a stereogenic, functionalized side chain, which can be easily modified to accommodate electronic and steric requirements. Based on a versatile synthetic procedure starting with optically active ferrocenes of the type cpFecp(PR2)(*CH(CH3)X) [X = OAc or NR2], a variety of donor atoms can be introduced into the side chain.4 These ferrocene based phosphine ligands have wide application in the stereoselective hydrogenation of substituted acetamidoacrylates, enol acetates, β-ketoesters and simple alkenes.
2. Useful as a ligand in Pd-catalyzed C-N bond-forming reactions.
3. Pd-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides.
4. Asymmetric hydrogenation of ketones and phosphinylketimines.
5. Michael addition of Grignard reagents to α,α-unsaturated esters and thioesters.
6. Boration of α,α-unsaturated esters and nitriles.
7. Reaction of aryl halides with ammonia.
8. Cu-catalyzed reduction of activated C=C bonds with PMHS.
9. Regio- and enantioselective hydroboration of vinyl arenes.
10. Rh-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes.

Chemical Properties

General Description