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88717

Sigma-Aldrich

(R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine

≥97%

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Synonym(s):
(2R)-1-[(1R)-1-(Dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)ferrocene (acc to CAS), (R)-(S)-Josiphos, Josiphos SL-J001-1
Empirical Formula (Hill Notation):
C36H44FeP2 · C2H5OH
CAS Number:
155806-35-2
Molecular Weight:
640.60
MDL number:
MFCD00800284
UNSPSC Code:
12352005
PubChem Substance ID:
24888985
NACRES:
NA.22

description

ethanol adduct

Quality Level

100

Assay

≥97%

form

powder

optical purity

ee: ≥99%

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][C]2P(c3ccccc3)c4ccccc4)P(C5CCCCC5)C6CCCCC6

InChI

1S/C31H39P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h4-5,10-14,19-27H,2-3,6-9,15-18H2,1H3;1-5H;/t25-;;/m1../s1

InChI key

HGTBZFMPHBAUCQ-KHZPMNTOSA-N

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General description

(R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ((R,S)-josiphos) is a chiral ferrocenyl diphosphine ligand.
sold in collaboration with Solvias AG

Application

It may be used in the preparation of cyclopentadienyliridium complexes, [IrCl(PP)]2 and [IrCp(PP)]. (Cp= cyclopentadienyl; PP= (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine)
Rhodium complex of (R)-(S)-JOSIPHOS can be used as a catalyst for the selective asymmetric hydrogenation of:       
  • Z-β-aryl-β-(enamido)phosphonates.     
  •  o-alkoxy tetrasubstituted enamides to yield β-amino alcohol analogs with excellent enantiomeric excess.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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)

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Iridium (I)-Catalyzed Asymmetric Intermolecular Hydroarylation of Norbornene with Benzamide.
Aufdenblatten R, et al.
Monatshefte fur Chemie / Chemical Monthly, 131(12), 1345-1350 (2000)
Rhodium complexes of (R)-Me-CATPHOS and (R)-(S)-JOSIPHOS: highly enantioselective catalysts for the asymmetric hydrogenation of (E)-and (Z)-β -aryl-β -(enamido) phosphonates
Doherty S, et al.
Tetrahedron Asymmetry, 20(12), 1437-1444 (2009)
Jingjing Meng et al.
Organic letters, 17(8), 1842-1845 (2015-03-27)
Rh/(R,S)-JosiPhos complex-catalyzed asymmetric hydrogenation of o-alkoxy tetrasubstituted enamides has been achieved, and it furnished a set of β-amino alcohol analogues in high yields and excellent enantiomeric excesses (>99% conversion, up to 99% ee).This method provides valuable chiral building blocks in
Privileged ligands
Aldrich Chemfiles, 6(8), 12-12 null

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