698393

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

• Synonym(s): (R,R)-Et-DUPHOS-Rh
• Empirical Formula (Hill Notation): C₃₁H₄₈F₃O₃P₂RhS
• CAS Number: 136705-77-6
• Molecular Weight: 722.62
• MDL number: MFCD00269860
• UNSPSC Code: 12352005
• PubChem Substance ID: 329761250
• NACRES: NA.22

Properties

• form: powder
• functional group: fluoro; phosphine; triflate
• 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

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