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  • 698393 - 1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate

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698393 Sigma-Aldrich

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

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

  • CAS Number 136705-77-6

  • Empirical Formula (Hill Notation) C31H48F3O3P2RhS

  • Molecular Weight 722.62

  •  MDL number MFCD00269860

  •  PubChem Substance ID 329761250

  •  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-;;;/m1.../s1
InChI key   HZLILTNLWVOBFS-KYOOHHHUSA-M

Description

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Catalyst for:
• Stereoselective synthesis of δ-amino acid derivatives via asymmetric hydrogenation of acetylaminopentenoic acid derivatives
• Stereoselective synthesis of manzacidins A and C via stereoselective hydrogenation
• Stereoselective synthesis of tetracyclic core of manzamine A via Rh-catalyzed asymmetric hydrogenation, diastereoselective Diels-Alder reaction, Eschenmoser-Tanabe fragmentation, Chang′s amide formation, and Hofmann rearrangement
• Asymmetric preparation of chiral Cbz-aminodifluorobutyric acid Me ester and its analogs
• Biphasic catalytic hydrogenations in ionic liquids with addition of water as a second solvent
• Preparation of cyclobutane-containing amino acids via asymmetric hydrogenations of cyclobutyl enamides
• Asymmetric preparation of both enantiomers of (dimethoxycoumaryl)alanine as suitable fluorescent peptide labels

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

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