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Merck
CN

900770

Berkessel ligand

98%, powder or crystals

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

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About This Item

Empirical Formula (Hill Notation):
C32H22F10N2O2
CAS Number:
2055467-90-6
Molecular Weight:
656.51
MDL number:
MFCD31560653
UNSPSC Code:
12161600
NACRES:
NA.22

Key Documents

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Product Name

Berkessel ligand, 98%

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

assay

98%

form

powder or crystals

reaction suitability

reagent type: ligand

Quality Level

100

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

Regulatory Information

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