(S)-(R)-JOSIPHOS Chemical Properties

alpha 

+360° (c 0.5, CHCl3)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Powder

color 

orange

Stability:

store cold

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

F 

10

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

(S)-(R)-JOSIPHOS Usage And Synthesis

Uses

(S)-(+)-1-[(R)-2-(diphenylphosphine)ferrocene]ethyldicyclohexylphosphine is a Josiphos-class chiral ferrocene phosphine ligand, a very practical and important ligand, second only to BINAP ligands in its pioneering role. It can be used in asymmetric organic synthesis reactions such as asymmetric hydroamination of olefins and Michael addition, and has been widely used in industrial production, playing an important role in the synthesis of many pharmaceuticals and fine chemicals.

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

(S)-(R)-JOSIPHOS(162291-02-3)Related Product Information

• 1,3-BIS(DIMETHYLPHOSPHINO)PROPANE
• JOSIPHOS SL-J011-1,JOSIPHOS SL-J011-2
• (R)-(S)-JOSIPHOS,(R)-(-)-1-[(S)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphineethanoladduct,min.97%(R)-(S)-JOSIPHOS,JOSIPHOS SL-J001-1
• TRIHEXYLPHOSPHINE
• TRIISOPROPYLPHOSPHINE
• JOSIPHOS SL-J005-1
• JOSIPHOS SL-J002-2
• JOSIPHOS SL-J002-1,Josiphos SL-J002-1, (2R)-1-[(1R)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene (acc to CAS)
• JOSIPHOS SL-J009-1
• DICYCLOHEXYLPHOSPHINE
• Ferrocene
• JOSIPHOS SL-J003-1
• Josiphos SL-J004-2, (1S)-1-(Dicyclohexylphosphino)-2-[(1S)-1-(diphenylphosphino)ethyl]ferrocene (acc to CAS),JOSIPHOS SL-J004-2
• (S)-(R)-JOSIPHOS
• 1,3-BIS(PHOSPHINO)PROPANE
• JOSIPHOS SL-J418-2
• JOSIPHOS SL-J013-1
• Josiphos SL-J003-2, (1S)-1-(Dicyclohexylphosphino)-2-[(1S)-1-(dicyclohexylphosphino)ethyl]ferrocene (acc to CAS)