698407

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

• Synonym(s): (S,S)-Et-DUPHOS-Rh
• Empirical Formula (Hill Notation): C₃₁H₄₈F₃O₃P₂RhS
• CAS Number: 142184-30-3
• Molecular Weight: 722.62
• MDL number: MFCD00269861
• UNSPSC Code: 12352005
• PubChem Substance ID: 329761251
• NACRES: NA.22

Properties

• form: powder
• 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

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

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

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 Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves