650862

Sigma-Aldrich

(R)-C3-TunePhos

Synonym(s):
(R)-1,13-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin
Empirical Formula (Hill Notation):
C39H32O2P2
CAS Number:
Molecular Weight:
594.62
MDL number:
PubChem Substance ID:

optical activity

[α]20/D -252±5°, c = 1 in chloroform

mp

153-161 °C (lit.)

SMILES string

C1COc2cccc(P(c3ccccc3)c4ccccc4)c2-c5c(OC1)cccc5P(c6ccccc6)c7ccccc7

InChI

1S/C39H32O2P2/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/h1-14,16-27H,15,28-29H2

InChI key

GTIXSUJKFAATAE-UHFFFAOYSA-N

Application

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation

Ligand used in:
  • Redox-neutral domino reaction of arylethynylbenzylidenearylpentynones catalyzed by gold catalyst
  • Asymmetric allylic O-alkylation
  • Asymmetric alkylation of racemic secondary phosphines catalyzed by ruthenium chiral diphosphine hydride complexes
  • Stereoselective preparation of cyclopropylcarboxaldehydes via Rh-catalyzed asymmetric hydroformylation of cyclopropenes
  • Rhodium-catalyzed asymmetric hydrogenations
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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
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)

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