162291-02-3

Basic information

• Product Name: (S)-(R)-JOSIPHOS
• Synonyms: (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ethanol adduct,97% (S)-(R)-JOSIPHOS;(S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ethanol adduct (S)-(R)-JOSIPHOS;(S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine >=97%;(S)-(+)-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDICYCLOHEXYLPHOSPHINE;(S)-1-[(1R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDICYCLOHEXYLPHOSPHINE;(S,S)-1-[1-(DICYCLOHEXYLPHOSPHINO)ETHYL]-2-(DIPHENYLPHOSPHINO)FERROCENE;(S)-(R)-JOSIPHOS;JOSIPHOS SL-J001-2
• CAS NO: 162291-02-3
• Molecular Formula: C₃₆H₄₄FeP₂
• Molecular Weight: 594.53
• Product Categories: Chiral Phosphine;Ferrocene Series;Josiphos Series;organophosphine ligand
• Mol File: 162291-02-3.mol
• Article Data: 1

Chemical Properties

• Appearance: orange/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Stability: store cold
• CAS DataBase Reference: (S)-(R)-JOSIPHOS(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(R)-JOSIPHOS(162291-02-3)
• EPA Substance Registry System: (S)-(R)-JOSIPHOS(162291-02-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 162291-02-3(Hazardous Substances Data)

Usage

Reactions

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. Pd-catalyzed, enantioselective, intramolecular α-substituted cyclic ketones: facile synthesis of functionalized chiral spirobicycles. Asymmetric boron conjugate addition of α,β-unsaturated carbonyl compounds catalyzed by CuOTf/Josiphos under non-alkaline conditions. Chiral amides via copper-catalyzed enantioselective conjugate addition. Ruthenium-catalyzed enantioselective synthesis of β-amino alcohols from 1,2-diols by “borrowing hydrogen”. Cobalt-catalyzed asymmetric addition of silylacetylenes to 1,1-disubstituted allenes.

Chemical Properties

Dark orange powder

General Description

sold in collaboration with Solvias AG

InChI:InChI=1/C31H39P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h4-5,10-14,19-27H,2-3,6-9,15-18H2,1H3;1-5H;/t25-;;/m0../s1

Upstream product

• 829-84-5 dicyclohexylphosphane 

Relevant articles and documents

Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands

The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.