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BINAP

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	Topics BINAP Topic Home BINAP is an acronym for the organophosphorus compound 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl. This chiral ligandLigand Summary In chemistry, a ligand is an atom, ion, or molecule that generally donates one or more of its electrons through a coordinat... is widely used in asymmetric synthesisChiral synthesis Chiral synthesis also called asymmetric synthesis or enantioselective synthesis is organic synthesis which prese... . It consists of a pair of 1-diphenylphosphinonaphthylNaphthalene Naphthalene is a crystalline, aromatic, white, solid hydrocarbon, best known as the primary ingredient of mothballs.... groups linked at the 2 positions (Figure 1). This C₂-symmetric framework lacks stereogenic atomStereocenter A stereocenter or stereogenic centre, in organic chemistry usually refers to a carbon atom in a chemical compound that has ... (see axial chirality Axial chirality Axial chirality is a special case of chirality in which a molecule does not possess an asymmetric carbon atom but an axis... ). The barrier to racemization is high due to steric hindrance that limits rotation about the bond linking the naphthyl rings. The dihedral angleDihedral angle In geometry, the angle between two planes is called their dihedral angle.... is approximately 90°. BINAP is used in organic synthesisOrganic synthesis Organic synthesis is the construction of organic molecules via chemical processes.... for enantioselective transformations catalyzed by its complexesComplex (chemistry) A complex in chemistry usually is used to describe molecules or ensembles formed by the combination of ligands and metal ion... of rutheniumRuthenium Ruthenium is a chemical element in the periodic table that has the symbol Ru and atomic number 44.... , rhodiumRhodium Rh redirects here. For other uses, see rh ... , and palladiumPalladium Palladium is a chemical element with symbol Pd and atomic number 46.... . As pioneered by Ryoji NoyoriRyoji Noyori Ryoji Noyori won the Nobel Prize in Chemistry in 2001.... and his co-workers, Rh complexes of BINAP are useful for the synthesis of (-)-mentholMenthol Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils.... . This synthetic method was industrialized by Takasago International Corporation. In part for this work, Noyori was awarded the 2001 Nobel Prize in ChemistryNobel Prize in Chemistry This is a list of Nobel Prize laureates in Chemistry from 1901 to 2005.... . BINAP is prepared from BINOL via its bis-triflate derivatives. Both the R and S enantiomerEnantiomer In chemistry, enantiomers are stereoisomers that are mirror images of each other.... s as well as the racemate are commercially available.