(S)-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]-ETHYLDI-TERT.-BUTYLPHOSPHINE

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. 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 ",$-unsaturated esters and thioesters.
6. Boration of ",$-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.
11. 1,2-Migrations in Pd-catalyzed Negishi couplings with JosiPhos ligands.

Orange powder

(S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine is β-boration catalyst; used in preparation of Sitagliptin β-Amino-2,4,5-trifluorobenzenebutanoic Acid derivatives intermediates via Grignard exchange reaction, cross coupling, β-boration, oxidation and Amination.

sold in collaboration with Solvias AG