698385

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

• Synonym(s): (S,S)-Et-DUPHOS-Rh
• Empirical Formula (Hill Notation): C₃₀H₄₈BF₄P₂Rh
• CAS Number: 213343-64-7
• Molecular Weight: 660.36
• UNSPSC Code: 12352005
• PubChem Substance ID: 329761249
• NACRES: NA.22

Properties

• form: powder
• SMILES string: [Rh+].F[B-](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.BF4.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)5;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;;/q;;-1;+1/b;2-1-,8-7-;;/t17-,18-,19-,20-;;;/m0.../s1
• InChI key: DSYBEQKPSKLNMC-ZCTOJWETSA-N

Description

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Catalyst for:

• Preparation of a key unit B precursor of cryptophycins via Horner-Wadsworth-Emmons reaction and asymmetric hydrogenation
• Preparation of constrained phenylalanine analogs via Heck reaction followed by asymmetric hydrogenation and cyclization steps
• Enantioselective preparation of N-benzyloxy-β-amino acid Me esters by hydrogenation of α-(benzyloxyaminomethyl)acrylate stereoisomers
• Preparation of fluoro amino acids as synthons for potent macrocyclic HCV NS3 protease inhibitors
• Stereoselective preparation of triply isotope-labeled Ser, Cys, and Ala
• Preparation of β-amino acids from asymmetric hydrogenation of α-(aminomethyl)acrylates
• Asymmetric hydrogenation of a-primary and secondary amino ketones and asymmetric synthesis of (-)-arbutamine and (-)-denopamine

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

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)