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659711

Sigma-Aldrich

(R)-C3-TunePhos-ruthenium complex

Synonym(s):

[Chloro(R)-C3-TunePhos)(p-cymene)ruthenium(II)] chloride

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About This Item

Empirical Formula (Hill Notation):
C49H46Cl2O2P2Ru
CAS Number:
905709-79-7
Molecular Weight:
900.81
MDL number:
MFCD07782001
UNSPSC Code:
12352101
PubChem Substance ID:
24884439
NACRES:
NA.22

mp

>300 °C

SMILES string

[Cl-].Cl[Ru+].C[C]1[CH][CH][C]([CH][CH]1)C(C)C.C2COc3cccc(P(c4ccccc4)c5ccccc5)c3-c6c(OC2)cccc6P(c7ccccc7)c8ccccc8

InChI

1S/C39H32O2P2.C10H14.2ClH.Ru/c1-5-16-30(17-6-1)42(31-18-7-2-8-19-31)36-26-13-24-34-38(36)39-35(41-29-15-28-40-34)25-14-27-37(39)43(32-20-9-3-10-21-32)33-22-11-4-12-23-33;1-8(2)10-6-4-9(3)5-7-10;;;/h1-14,16-27H,15,28-29H2;4-8H,1-3H3;2*1H;/q;;;;+2/p-2

InChI key

BOERIKXMDOKSHH-UHFFFAOYSA-L

Application

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation
Provides comparable or superior enantioselectivities and catalytic abilities to BINAP in Ru-catalyzed asymmetric hydrogenations of β-keto esters, cyclic β-(acylamino)acrylates and α-phthalimide ketones.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Wenjun Tang et al.
Journal of the American Chemical Society, 125(32), 9570-9571 (2003-08-09)
Hydrogenation of a series of cyclic beta-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an
Synthesis of chiral bisphosphines with tunable bite angles and their applications in asymmetric hydrogenation of beta-ketoesters.
Z Zhang et al.
The Journal of organic chemistry, 65(19), 6223-6226 (2000-09-16)
Aiwen Lei et al.
Journal of the American Chemical Society, 126(6), 1626-1627 (2004-02-12)
A new type of alpha-phthalimide ketones was hydrogenated in excellent enantioselectivity by using a Ru-(C3-TunePhos) complex as the catalyst. Up to 10 000 turnovers have been achieved in more than 99% ee in the hydrogenation reaction. A dynamic kinetic resolution

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