Walphos SL-W006-2 - CAS 849925-21-9

Walphos SL-W006-2 is a chiral phosphine ligand for enantioselective synthesis with high yield and high enantioselective results.

Catalog Number

849925-21-9

CAS

849925-21-9

Synonyms

(1R)-1-[(1S)-1-[Bis(3,5-dimethylphenyl)phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene (acc to CAS), Walphos SL-W006-2

Molecular Weight

714.63

Molecular Formula

C46H44FeP2

Product Information

Canonical SMILES

CC1=CC(C)=CC(P(C2=CC(C)=CC(C)=C2)[C@H]([C@-]34[Fe+2]56789%10(C%11=C46[H])([C-]%12C7=C8C9=C%10%12)C%11([H])=C35C%13=C(C=CC=C%13)P(C%14=CC=CC=C%14)C%15=CC=CC=C%15)C)=C1

InChI

InChI=1S/C41H39P2.C5H5.Fe/c1-29-23-30(2)26-36(25-29)42(37-27-31(3)24-32(4)28-37)33(5)38-20-14-21-39(38)40-19-12-13-22-41(40)43(34-15-8-6-9-16-34)35-17-10-7-11-18-35;1-2-4-5-3-1;/h6-28,33H,1-5H3;1-5H;

InChI Key

SPJXDOOLGLNVOP-UHFFFAOYSA-N

MDL

MFCD08561126

Storage

Inert atmosphere. Keep cold.

Safety Information

Signal Word

Warning

Precautionary Statement

P261 - P305+P351+P338

Hazard Statements

H302 - H315 - H319 - H335

Reference Reading

1. Walphos versus biferrocene-based walphos analogues in the asymmetric hydrogenation of alkenes and ketones.

Manuela A Groß, Kurt Mereiter, Yaping Wang, Afrooz Zirakzadeh, Walter Weissensteiner. Organometallics. 2014 Apr 28; 33(8): 1945-1952. DOI: 10.1021/om401074a. PMID: 24795493.

Two representative Walphos analogues with an achiral 2,2″-biferrocenediyl backbone were synthesized. These diphosphine ligands were tested in the rhodium-catalyzed asymmetric hydrogenation of several alkenes and in the ruthenium-catalyzed hydrogenation of two ketones. The results were compared with those previously obtained on using biferrocene ligands with aC2-symmetric 2,2″-biferrocenediyl backbone as well as with those obtained with Walphos ligands. The application of one newly synthesized ligand in the hydrogenation of 2-methylcinnamic acid gave (R)-2-methyl-3-phenylpropanoic acid with full conversion and with 92% ee. The same ligand was used to transform 2,4-pentanedione quantitatively and diastereoselectively into (S,S)-2,4-pentanediol with 98% ee.

The molarity calculator equation

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

Mass