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277306-29-3

277306-29-3 Structure

277306-29-3 Structure
IdentificationBack Directory
[Name]

(S)-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]-ETHYLDI-TERT.-BUTYLPHOSPHINE
[CAS]

277306-29-3
[Synonyms]

(S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine
(S)-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]-ETHYLDI-TERT.-BUTYLPHOSPHINE
(S)-(-)-1-[(Rp)-2-(Diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphine
(S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine >=97%
(S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphine,min.97%
(S)-(+)-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE, MIN. 97%
(2R)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene
(s,s)-1-[1-(di-tert-butylphosphino)ethyl]-2-(diphenylphosphino]ferrocene (acc to cas)
Josiphos SL-J002-2, (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene (acc to CAS)
[Molecular Formula]

C27H35P2.C5H5.Fe
[MDL Number]

MFCD01074443
[MOL File]

277306-29-3.mol
[Molecular Weight]

542.461
Chemical PropertiesBack Directory
[alpha ]

+412° ±15° (c 0.5, CHCl3)
[storage temp. ]

Inert atmosphere,2-8°C
[form ]

Powder
[color ]

orange
[Optical Rotation]

[α]20/D +410±15°, c = 0.5 in chloroform
[InChI]

1S/C27H35P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h8-21H,1-7H3;1-5H;/t21-;;/m0../s1
[InChIKey]

STAGMXYQPGLLTD-FGJQBABTSA-N
[SMILES]

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@@H]([C]2[CH][CH][CH][C]2P(c3ccccc3)c4ccccc4)P(C(C)(C)C)C(C)(C)C
Hazard InformationBack Directory
[Chemical Properties]

Orange powder
[Uses]

(S)-1-[(RP)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine is β-boration catalyst; used in preparation of Sitagliptin β-Amino-2,4,5-trifluorobenzenebutanoic Acid derivatives intermediates via Grignard exchange reaction, cross coupling, β-boration, oxidation and Amination.
[General Description]

sold in collaboration with Solvias AG
Safety DataBack Directory
[Safety Statements ]

22-24/25
[WGK Germany ]

3
[F ]

10
[HS Code ]

29319090
[Storage Class]

11 - Combustible Solids
Questions And AnswerBack Directory
[Reaction]

  1. Ferrocenylphosphine ligands of the type cpFecp(PR2)(*CH(CH3)PR'2) are a class of asymmetric ligands developed at Solvias in Basel, Switzerland . Ligands of this type are currently used industrially in the stereoselective synthesis of commercial products. A unique feature of these bidentate ligands is the presence of a fixed phosphine moiety and a stereogenic, functionalized side chain, which can be easily modified to accommodate electronic and steric requirements. Based on a versatile synthetic procedure starting with optically active ferrocenes of the type cpFecp(PR2)(*CH(CH3)X) [X = OAc or NR2], a variety of donor atoms can be introduced into the side chain. These ferrocene based phosphine ligands have wide application in the stereoselective hydrogenation of substituted acetamidoacrylates, enol acetates, β-ketoesters and simple alkenes.
  2. Useful as a ligand in Pd-catalyzed C-N bond-forming reactions.
  3. Pd-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides.
  4. Asymmetric hydrogenation of ketones and phosphinylketimines.
  5. Michael addition of Grignard reagents to ",$-unsaturated esters and thioesters.
  6. Boration of ",$-unsaturated esters and nitriles.
  7. Reaction of aryl halides with ammonia.
  8. Cu-catalyzed reduction of activated C=C bonds with PMHS.
  9. Regio- and enantioselective hydroboration of vinyl arenes.
  10. Rh-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes.
  11. 1,2-Migrations in Pd-catalyzed Negishi couplings with JosiPhos ligands.
Reactions of 277306-29-3_1
Reactions of 277306-29-3_2
Reactions of 277306-29-3_3
Spectrum DetailBack Directory
[Spectrum Detail]

(S)-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]-ETHYLDI-TERT.-BUTYLPHOSPHINE(277306-29-3)1HNMR
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