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88717 Sigma-Aldrich

(R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine

≥97%

Synonym: (2R)-1-[(1R)-1-(Dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)ferrocene (acc to CAS), (R)-(S)-Josiphos, Josiphos SL-J001-1

  • CAS Number 155806-35-2

  • Empirical Formula (Hill Notation) C36H44FeP2 · C2H5OH

  • Molecular Weight 640.60

  •  MDL number MFCD00800284

  •  PubChem Substance ID 24888985

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Josiphos Ligands, Privileged Ligands and Complexes,
Quality Level   100
description   ethanol adduct
assay   ≥97%
optical purity   ee: ≥99%
SMILES string   [Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][C]2P(c3ccccc3)c4ccccc4)P(C5CCCCC5)C6CCCCC6
InChI   1S/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-;;/m1../s1
InChI key   HGTBZFMPHBAUCQ-KHZPMNTOSA-N

Description

General description

(R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ((R,S)-josiphos) is a chiral ferrocenyl diphosphine ligand.

sold in collaboration with Solvias AG

Application

It may be used in the preparation of cyclopentadienyliridium complexes, [IrCl(PP)]2 and [IrCp(PP)]. (Cp= cyclopentadienyl; PP= (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine)

Rhodium complex of (R)-(S)-JOSIPHOS can be used as a catalyst for the selective asymmetric hydrogenation of:       
•  Z-β-aryl-β-(enamido)phosphonates.     
•  o-alkoxy tetrasubstituted enamides to yield β-amino alcohol analogs with excellent enantiomeric excess.

Packaging

1, 5 g in glass bottle

100, 500 mg in glass bottle

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Antonio Togni - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Antonio Togni - Professor Product Portal
Keywords: Asymmetric synthesis, Catalysis, Chemical biology, Herbicides, Hydrogenations, Ligands, Nuclear magnetic resonance spectroscopy, Spectroscopy

Solvias® Ligand Portfolio for Enantioselective Hydrogenation

Today's Solvias Ligand Portfolio has its roots in the development of the Josiphos ligands and the successful implementation in the (S)-metolachlor process—the largest industrial enantioselective manu...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 14.
Keywords: Alkylations, Aminations, Asymmetric catalysis, Asymmetric synthesis, Building blocks, Catalysis, Coupling reactions, Crystallization, Grignard Reaction, Heck Reaction, Herbicides, Hydroformylations, Hydrogenations, Infrared spectroscopy, Kumada Coupling, Ligands, Michael Addition, Reductions, Supercritical fluid chromatography

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Solvias Chiral Phosphine Ligands - Toolkit for Asymmetric Catalysis

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Keywords: Asymmetric catalysis, Asymmetric synthesis, Catalysis, Individual protein Immunoprecipitation, Ligands

Peer-Reviewed Papers
15

References

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