(S)-(-)-BINAP

Application

The purpose of (S)-(-)-BINAP is to serve as a chiral ligand for metal-mediated asymmetric catalysis, offering crucial functionality in various chemical processes. This white to light yellow crystalline powder is integral in enantioselective and diastereoselective reactions, such as unpoled carbonyl allylation and SN2 halogenation of hydroxy groups. In the synthesis of organophosphine oxides, which are explored as antitumor agents, (S)-(-)-BINAP plays a pivotal role. It is utilized in forming BINAP complexes and examining the conformational flexibility of BINAP chelates. In combination with dichloro(1,5-cyclooctadiene)ruthenium, (S)-(-)-BINAP forms precursors to NOYORI CATALYST SYSTEMS, renowned for their exceptional catalytic activity and enantioselectivity in the hydrogenation of diverse substrates, particularly functionalized ketones with various substituents. Moreover, (S)-(-)-BINAP is a valuable ligand in asymmetric Heck processes, and its efficacy extends to palladium-catalyzed asymmetric arylation of ketones, rhodium-catalyzed 1,4-additions to enones, and hydroamination of styrene derivatives. It supports silver-catalyzed asymmetric Sakuri-Hosomi allylation, Mukaiyama aldol reaction, kinetic resolution of enynes, and asymmetric hydroboration of cyclopropenes, among others. Its palladium-catalyzed manifestation aids the synthesis of chiral allenes and facilitates the reduction of aryl ketones, β-keto esters, and α-amino ketones. Characterized by its use in asymmetric hydrogenation, hydroformylation of olefins, and isomerizations of allyls, (S)-(-)-BINAP is indispensable in reaction processes such as the tandem Heck reaction-carbanion capture process for synthesizing a tricyclic sesquiterpene, and in ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.