Walphos SL-W003-2 - CAS 849925-19-5

Walphos SL-W003-2 is a chiral phosphine ligand for enantioselective synthesis with high yield and high enantioselective results.

Catalog Number

849925-19-5

CAS

849925-19-5

Synonyms

(1R)-1-[(1S)-1-(Dicyclohexylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene (acc to CAS), Walphos SL-W003-2

Molecular Weight

670.62

Molecular Formula

C42H48FeP2

Product Information

Canonical SMILES

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][C]2c3ccccc3P(c4ccccc4)c5ccccc5)P(C6CCCCC6)C7CCCCC7

InChI

InChI=1S/C37H43P2.C5H5.Fe/c1-29(38(30-17-6-2-7-18-30)31-19-8-3-9-20-31)34-26-16-27-35(34)36-25-14-15-28-37(36)39(32-21-10-4-11-22-32)33-23-12-5-13-24-33;1-2-4-5-3-1;/h4-5,10-16,21-31H,2-3,6-9,17-20H2,1H3;1-5H;

InChI Key

OBVCATYDMKRFLP-UHFFFAOYSA-N

Purity

≥97%

MDL

MFCD04117711

Storage

Inert atmosphere. Keep cold.

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P261 - P305+P351+P338

Hazard Statements

H302 - H315 - H319 - H335

Reference Reading

1. Biferrocene-based diphosphine ligands: synthesis and application of walphos analogues in asymmetric hydrogenations.

Manuela A Groß, Kurt Mereiter, Felix Spindler, Yaping Wang, Afrooz Zirakzadeh, Walter Weissensteiner. Organometallics. 2013 Feb 25; 32(4): 1075-1084. DOI: 10.1021/om3012147. PMID: 23457421.

A total of four biferrocene-based Walphos-type ligands have been synthesized, structurally characterized, and tested in the rhodium-, ruthenium- and iridium-catalyzed hydrogenation of alkenes and ketones. Negishi coupling conditions allowed the biferrocene backbone of these diphosphine ligands to be built up diastereoselectively from the two nonidentical and nonracemic ferrocene fragments (R)-1-(N,N-dimethylamino)ethylferrocene and (SFc)-2-bromoiodoferrocene. The molecular structures of (SFc)-2-bromoiodoferrocene, the coupling product, two ligands, and the two complexes ([PdCl2(L)] and [RuCl(p-cymene)(L)]PF6) were determined by X-ray diffraction. The structural features of complexes and the catalysis results obtained with the newly synthesized biferrocene-based ligands were compared with those of the corresponding Walphos ligands.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass