(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Reaction

1. (R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.
2. Useful ligand in asymmetric Heck processes.
3. Ligand employed in palladium-catalyzed asymmetric arylation of ketones.
4. Ligand employed in rhodium-catalyzed 1,4-additions to enones.
5. Ligand employed in palladium-catalyzed hydroamination of styrene derivatives.
6. Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction.
7. Ligand employed in rhodium-catalyzed kinetic resolution of enynes.
8. Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes.
9. Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers.
10. Ligand employed in palladium-catalyzed synthesis of chiral allenes.

Chemical Properties

white to light yellow crystal powde

Uses

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.

Uses

Reactant involved in:

• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

Uses

Chiral ligand for metal mediated asymmetric catalysis.