(S)- and (R)-BINAP

Ball and stick model of BINAP viewed as above

In organic chemistry, BINAP, an acronym used for 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, is an important chiral ligand widely used in asymmetric synthesis. It consists of two naphthyl groups linked by a single bond with diphenylphosphino groups at the end of each naphthyl group (Figure 1). This framework is chiral, yet it has no stereogenic center (see axial chirality ). Rotation about the single bond binding the two naphthyl groups is restricted because of the rigidity of their π systems. Therefore the angle made by the two π planes is fixed to approximately 90˚ and two separate enantiomers exist, as shown in the figure: Image File history File links BINAP.png Images of (S)- and (R)- BINAP Permission is granted to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... Image File history File links BINAP.png Images of (S)- and (R)- BINAP Permission is granted to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... Image File history File links Size of this preview: 713 × 600 pixelsFull resolution (1000 × 841 pixel, file size: 133 KB, MIME type: image/png) Chemical structure of BINAP created with ChemDraw. ... Image File history File links Size of this preview: 713 × 600 pixelsFull resolution (1000 × 841 pixel, file size: 133 KB, MIME type: image/png) Chemical structure of BINAP created with ChemDraw. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... It has been suggested that this article or section be merged with Backronym and Apronym (Discuss) Acronyms and initialisms are abbreviations, such as NATO, laser, and ABC, written as the initial letter or letters of words, and pronounced on the basis of this abbreviated written form. ... Optical isomerism is a form of isomerism (specifically stereoisomerism) where the two different isomers are the same in every way except being non-superposable mirror images of each other. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a... The two optical isomers of bromochlorofluoromethane Chiral synthesis (also called asymmetric synthesis) is organic synthesis which preserves or introduces a desired chirality. ... Naphthalene (not to be confused with naphtha) (also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or naphthene), is a crystalline, aromatic, white, solid hydrocarbon, best known as the primary ingredient of mothballs. ... Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. ... Naphthalene (not to be confused with naphtha) (also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or naphthene), is a crystalline, aromatic, white, solid hydrocarbon, best known as the primary ingredient of mothballs. ... A stereocenter in organic chemistry generally refers to a carbon atom in a chemical compound that has four different types of atoms or groups of atoms attached to it. ... Term used to refer to stereoisomerism resulting from the non-planar arrangement of four groups in pairs about a chirality axis. ... Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. ... Naphthalene (not to be confused with naphtha) (also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or naphthene), is a crystalline, aromatic, white, solid hydrocarbon, best known as the primary ingredient of mothballs. ... A chemically conjugated system, is a system of atoms covalently bonded with alternating single and double bonds (e. ... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ...

This chiral structure of BINAP enables highly enantioselective reactions in organic synthesis. Enantioselective organic reactions catalyzed by BINAP complexes using transition metals such as ruthenium, rhodium, and palladium have been reported, with asymmetric hydrogenation catalyzed by Rh- and Ru-BINAP being pioneered by Ryoji Noyori, winner of the 2001 Nobel Prize in Chemistry, and his co-workers. The most important and well-known work in their studies is asymmetric synthesis of (-)-menthol, which is extensively used as a flavoring ingredient, catalyzed by Rh-BINAP. This synthetic method was industrialized by Takasago International Corporation, which provides (-)-menthol to pharmaceutical and food companies worldwide. Optical isomerism is a form of isomerism (specifically stereoisomerism) where the two different isomers are the same in every way except being non-superposable mirror images of each other. ... In chemistry two stereoisomers are said to be enantiomers if one can be superimposed on the mirror image of the other. ... Organic synthesis is the construction of organic molecules via chemical processes. ... In chemistry two stereoisomers are said to be enantiomers if one can be superimposed on the mirror image of the other. ... Synthesis of copper(II)-tetraphenylporphine, a metal complex, from tetraphenylporphine and copper(II) acetate monohydrate. ... In chemistry, the term transition metal (sometimes also called a transition element) has two possible meanings: It commonly refers to any element in the d-block of the periodic table, including zinc, cadmium and mercury. ... General Name, Symbol, Number Ruthenium, Ru, 44 Chemical series transition metals Group, Period, Block 8, 5, d Appearance silvery white metallic Atomic mass 101. ... General Name, Symbol, Number rhodium, Rh, 45 Chemical series transition metals Group, Period, Block 9, 5, d Appearance silvery white metallic Atomic mass 102. ... General Name, Symbol, Number palladium, Pd, 46 Chemical series transition metals Group, Period, Block 10, 5, d Appearance silvery white metallic Standard atomic weight 106. ... Hydrogenation is a class of chemical reactions which result an addition of hydrogen (H2) usually to unsaturated organic compounds. ... Ryoji Noyori (野依良治) (born September 3, 1938) won the Nobel Prize in Chemistry in 2001. ... This is a list of Nobel Prize laureates in Chemistry from 1901 to 2006. ... The two optical isomers of bromochlorofluoromethane Chiral synthesis (also called asymmetric synthesis) is organic synthesis which preserves or introduces a desired chirality. ... Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. ... Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. ... Pharmaceutics is the discipline of pharmacy which deals with all facets of the process of turning a new chemical entity (NCE) into a medication able to be safely and effectively used by patients in the community. ...

BINAP is prepared from BINOL (1,1'-bi-2-naphthol) via its bis-triflate derivatives. Both the R and S enantiomers as well as the racemate are commercially available. 1,1-bi-2-naphthol or 1,1-binaphthol or 1,1-binaphthalene-2,2-diol or BINOL is an organic compound that is often used as a ligand for transition-metal catalysed asymmetric synthesis. ... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ...

References

1. ^  "Binap: An industrial approach to manufacture" -dead link.
2. BINAP synthesis in Organic Syntheses, Coll. Vol. 10, p.112 (2004); Vol. 76, p.6 (1999) Article.
3. Asymmetric hydrogenation of methyl 3-oxobutanoate to (R)-Methyl 3-hydroxybutanoate with a ruthenium BINAP catalyst in Organic Syntheses, Coll. Vol. 9, p.589 (1998); Vol. 71, p.1 (1993) Article.

Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Hydrogenation is a class of chemical reactions which result an addition of hydrogen (H2) usually to unsaturated organic compounds. ... Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...

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