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650862 Sigma-Aldrich

(R)-C3-TunePhos

Synonym: (R)-1,13-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Chiral Quest Ligands and Complexes, Privileged Ligands and Complexes More...
InChI Key   GTIXSUJKFAATAE-UHFFFAOYSA-N
optical activity   [α]20/D -252±5°, c = 1 in chloroform
mp   153-161 °C (lit.)

Description

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.

Packaging

500 mg in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

ChiralQuest Phosphine Ligands - Aldrich ChemFiles 2006, 6.8, 10.

One of the most efficient methods for constructing chiral compounds is asymmetric hydrogenation. Catalytic asymmetric hydrogenations are among the most widely used industrial catalytic processes, due...
Aldrich ChemFiles 2006, 6.8, 10.
Keywords: Asymmetric catalysis, Asymmetric synthesis, Catalysis, Chemfiles, Hydrogenations, Ligands, Methods, Reductions, transformation

ChiralQuest Phosphine Ligands - ChemFiles Volume 5 Article 10

The field of asymmetric catalysis has been primarily represented by methodologies that have focused on incorporating hydrogen in a stereoselective manner into achiral molecules, especially in industr...
ChemFiles Volume 5 Article 10
Keywords: Applications, Asymmetric catalysis, Asymmetric synthesis, Catalysis, Hydrogenations, Ligands, Reductions, transformation

ChiralQuest Phosphine Ligands and Complexes

Professor Xumu Zhang at Penn State has made remarkable advances by creating a toolbox of chiral phosphines which can be used on a variety of substrates, some of which have been historically resistant...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 47.
Keywords: Asymmetric catalysis, Asymmetric synthesis, Catalysis, Chemfiles, Cyclizations, Hydrogenations, Ligands, Reductions

Related Content

Chiral Quest Phosphine Ligands in chemical Synthesis

One of the most efficient methods for constructing chiral compounds is asymmetric hydrogenation. Catalytic asymmetric hydrogenations are among the most widely used industrial catalytic processes, due...
Keywords: Asymmetric synthesis, Catalysis, Hydrogenations, Ligands, Reductions, transformation

Peer-Reviewed Papers
15

References

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