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Berkessel ligand

ALDRICH/900770 - 98%

Synonym: 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

CAS Number: 2055467-90-6
Empirical Formula (Hill Notation): C32H22F10N2O2
Molecular Weight: 656.51
MDL Number: MFCD31560653
Linear Formula: C32H22F10N2O2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-900770-100MG 100 mg
 $168.00
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assay 98%
form powder or crystals
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
Quality Level 100 
reaction suitability reagent type: ligand
SMILES string Fc1c(c(c(c(c1F)F)c2c(c(ccc2)CN[C@@H]3[C@@H](CCCC3)N=Cc4c(c(ccc4)c5c(c(c(c(c5F)F)F)F)F)O)O)F)F
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 
Packaging: 100 mg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Purity 98%
UNSPSC 12161600

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