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  • 698407 - 1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate

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698407 Sigma-Aldrich

1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate

Synonym: (S,S)-Et-DUPHOS-Rh

  • CAS Number 142184-30-3

  • Empirical Formula (Hill Notation) C31H48F3O3P2RhS

  • Molecular Weight 722.62

  •  MDL number MFCD00269861

  •  PubChem Substance ID 329761251

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, DuPhos/BPE, Privileged Ligands and Complexes More...
Quality Level   100
SMILES string   [Rh+].[O-]S(=O)(=O)C(F)(F)F.C1CC=CCCC=C1.CC[C@H]2CC[C@H](CC)P2c3ccccc3P4[C@@H](CC)CC[C@@H]4CC
InChI   1S/C22H36P2.C8H12.CHF3O3S.Rh/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4;1-2-4-6-8-7-5-3-1;2-1(3,4)8(5,6)7;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;(H,5,6,7);/q;;;+1/p-1/b;2-1-,8-7-;;/t17-,18-,19-,20-;;;/m0.../s1
InChI key   HZLILTNLWVOBFS-ZCTOJWETSA-M

Description

General description

1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate is an electron-rich C2 symmetric bis(phospholane) ligand for enantioselective catalytic reactions.

Application

(S,S)-Et-DUPHOS-Rh may be used as an efficient catalyst in the synthesis of (S)-2-quinolylalanine via asymmetric hydrogenation.

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Catalyst involved in:
• Oxidation of the δ-position via ruthenium catalysis
• Stereoselective hydrogenation reactions of dehydroamino acid esters and macrocyclic peptideomimetics
• Synthesis of cyclopeptide alkaloid mucronine E, fluoro-containing amino acids, and labeled protease inhibitors

Packaging

50, 250 mg in amber glass bottle

Legal Information

Sold in collaboration with Kanata Chemical Technologies Inc. for research purposes only. These compounds were made and sold under license from E.I. du Pont de Nemours and Company, which license does not include the right to use the compounds in producing products for sale in the pharmaceutical field.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
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

DuPhos and BPE Phospholane Ligands and Complexes

In the early 1990s, Burk and coworkers developed new electron-rich C2 symmetric bis(phospholane) ligands. The modular nature of these ligands allowed for variation of both phosphane substituent and b...
William Sommer and Daniel Weibel
ChemFiles 2008, 8.2, 34.
Keywords: Aminations, Asymmetric catalysis, Asymmetric synthesis, Building blocks, Catalysis, Crotylborations, Hydrogenations, Ligands, Reductions, Reductive aminations

Peer-Reviewed Papers
15

References

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