900770

Berkessel ligand

98%

• Synonym(s): 2′,3′,4′,5′,6′-Pentafluoro-3-({(E)-[(1R,2S)-2-{[(2′,3′,4′,5′,6′-pentafluoro-2-hydroxy[1,1′-biphenyl]-3-yl)methyl]amino}cyclohexyl]imino}methyl)[1,1′-biphenyl]-2-ol, cis-1,2-Diaminocyclohexane salalen ligand, cis-DACH salalen ligand, Bis(pentafluorophenyl) salalen ligand
• Empirical Formula (Hill Notation): C₃₂H₂₂F₁₀N₂O₂
• CAS Number: 2055467-90-6
• Molecular Weight: 656.51
• MDL number: MFCD31560653
• UNSPSC Code: 12161600
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 98%
• form: powder or crystals
• reaction suitability: reagent type: ligand
• SMILES string: Fc1c(c(c(c(c1F)F)c2c(c(ccc2)CN[C@@H]3[C@@H](CCCC3)\N=C\c4c(c(ccc4)c5c(c(c(c(c5F)F)F)F)F)O)O)F)F
• InChI: 1S/C32H22F10N2O2/c33-21-19(22(34)26(38)29(41)25(21)37)15-7-3-5-13(31(15)45)11-43-17-9-1-2-10-18(17)44-12-14-6-4-8-16(32(14)46)20-23(35)27(39)30(42)28(40)24(20)36/h3-8,11,17-18,44-46H,1-2,9-10,12H2/b43-11+/t17-,18+/m1/s1
• InChI key: NLJCGFOPEQFWQJ-XOZUKITKSA-N

Description

Application

Developed by Albrecht Berkessel′s lab, this is the first catalyst system that allows catalytic enantioselective epoxidation of non-conjugated terminal double bonds with hydrogen peroxide as the oxidant. Eradicating multiple steps and kinetic resolution, this chiral ligand, when used with Ti(OiPr)₄ provides a one-step route to enantiopure epoxides that are important intermediates for synthesis of bioactive compounds. Catalyst is recyclable under some conditions. For best results, pentafluorobenzoic acid (P5360) or tetra-n-butylammonium hydrogensulfate (155837) is recommended as a co-catalyst.

Other Notes

Titanium cis-1,2-Diaminocyclohexane Salalen Catalysts of Outstanding Activity and Enantioselectivity for the Asymmetric Epoxidation of Nonconjugated Terminal Olefins with Hydrogen Peroxide

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3