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65671

Sigma-Aldrich

(R)-1-{(RP)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis-(trifluoromethyl)phenyl]phosphine

≥97%

Synonym(s):

(1S)-1-[(1R)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene, Walphos SL-W001-2

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About This Item

Empirical Formula (Hill Notation):
C46H32F12FeP2
CAS Number:
387868-06-6
Molecular Weight:
930.52
MDL number:
MFCD08561122
UNSPSC Code:
12352101
PubChem Substance ID:
24884219
NACRES:
NA.22

Quality Level

100

Assay

≥97%

optical purity

ee: ≥99%

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@@H]([C]2[CH][CH][CH][C]2c3ccccc3P(c4ccccc4)c5ccccc5)P(c6cc(cc(c6)C(F)(F)F)C(F)(F)F)c7cc(cc(c7)C(F)(F)F)C(F)(F)F

InChI

1S/C41H27F12P2.C5H5.Fe/c1-25(34-16-10-17-35(34)36-15-8-9-18-37(36)55(30-11-4-2-5-12-30)31-13-6-3-7-14-31)54(32-21-26(38(42,43)44)19-27(22-32)39(45,46)47)33-23-28(40(48,49)50)20-29(24-33)41(51,52)53;1-2-4-5-3-1;/h2-25H,1H3;1-5H;/t25-;;/m0../s1

InChI key

LKNKYBWIZNAXBY-WLOLSGMKSA-N

General description

The product is an air-stable and non-hygroscopic Solvias chiral phosphine ligand.

Application

Walphos SL-W001-2, in the presence of a ruthenium catalyst may be used as a ligand in the following processes:
  • Asymmetric hydrogenation of IPCA-D, a cinnamic acid derivative.
  • Addition of 3,5-difluorophenylketimine to 4-methoxyphenylboronic acid to form the corresponding tertiary substituted cyclic sulfamate derivative with high enantioselctivity.2

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

sold in collaboration with Solvias AG

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Enantioselective Rh (I)-catalyzed addition of arylboronic acids to cyclic ketimines.
Kong J, et al.
Organic Letters, 17(22), 5520-5523 (2015)
Afrooz Zirakzadeh et al.
Organometallics, 33(8), 1945-1952 (2014-05-06)
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

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