BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an organophosphorus compound. This chiral diphosphine ligand is widely used in asymmetric synthesis...
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steric hindrance of the groups, as in substituted biaryl compounds such as BINAP, or by torsional stiffness of the bonds, as in the C=C double bonds in allenes...
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the BINAP-Ru-diamine system. The dihalide form of the catalyst is converted to the catalysts by reaction of H2 in the presence of base: RuCl2(BINAP)(diamine)...
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Lewis acid catalysis (section BINAP)
backbone. BINAP chelates onto a metal (usually a late transition metal) to form a C2-symmetric complex. As shown below in the structure of an (R)-BINAP ruthenium...
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dextrorotary one. BINOL is a precursor for another chiral ligand called BINAP. The volumetric mass density of the two enantiomers is 0.62 g cm−3.[citation...
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chirality). When the barrier to racemization is high, as illustrated by the BINAP ligands, the phenomenon becomes of practical value in asymmetric synthesis...
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phosphine ligands such as 1,2-bis(diphenylphosphino)ethane (Ph2PC2H4PPh2) and BINAP. via its bistriflate derivatives. Both the (R)- and (S)-enantiomers, as...
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particularly those based on the BINAP ligand. Asymmetric hydrogenation of an alkene in the presence of ((S)-BINAP)Ru(OAc)2 is used for the commercial...
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Noyori, Ryoji (1995). "Asymmetric Hydrogenation of Allylic Alcohols Using BINAP–Ruthenium Complexes: (S)-(−)-citronellol". Organic Syntheses. 72: 74. doi:10...
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myrcene, which undergoes asymmetric isomerisation in the presence of a BINAP rhodium complex to give (after hydrolysis) enantiomerically pure R-citronellal...
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used to reduce benzene to cyclohexane. The complex of a rhodium ion with BINAP is a widely used chiral catalyst for chiral synthesis, as in the synthesis...
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basic conditions. To select for one of the four possible stereoisomers, a BINAP-Ru catalyst is used to control the outcome of the reaction through the steric...
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Ru(BINAP) catalyst. The configuration of the new stereocenter is predictable using the stereochemical model developed for hydrogenations employing BINAP...
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catalysts are often chelated complexes. A representative example is the use of BINAP (a bidentate phosphine) in Noyori asymmetric hydrogenation and asymmetric...
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allylic alcohols by asymmetric hydrogenation of the olefin. Utilizing the Ru[BINAP] complex, selective hydrogenation can give high ee's of the unsaturated...
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of ketones was demonstrated with ruthenium-based complexes of BINAP. Even though the BINAP-Ru dihalide catalyst could reduce functionalized ketones, the...
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synthesized efficiently from hydroxyacetone by using catalysts based on BINAP-ruthenium complexes, in Noyori asymmetric hydrogenation: One of the most...
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be obtained by asymmetric hydrogenation of tiglic acid using a ruthenium-BINAP catalyst. The compound and its enantiomers react as typical carboxylic acids:...
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to 1,1-binaphthol: Such compounds are intermediates in the synthesis of BINAP and its derivatives. Copper(II) chloride dihydrate promotes the hydrolysis...
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optically stable. Some derivatives, as well as related molecules such as BINAP, find application as ligands in asymmetric synthesis. In the case of unsubstituted...
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(1999). "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Organic Syntheses. 76: 6. doi:10.15227/orgsyn.076.0006. Dell'Amico, Daniela...
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palladium(II) acetate. Typical supporting ligands are triphenylphosphine, PHOX, and BINAP. Typical bases are triethylamine, potassium carbonate, and sodium acetate...
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example, Noyori asymmetric hydrogenation with BINAP/Ru requires a β-ketone, although another catalyst, BINAP/diamine-Ru, widens the scope to α,β-alkenes...
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Kiyomi (October 22, 2005). "Facile Preparation of a New BINAP-Based Building Block, 5,5'-DiiodoBINAP, and Its Synthetic Application". The Journal of Organic...
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tributaries of this river are Sapanatirtha Khola, Sangle Khola, Lhora Khola, and Binap Falls. Bisnap[clarification needed] fall locates at the Shivapuri National...
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yields and excellent enantioselectivities using Cu-Al hydrotalcite and BINAP has opened up a new perspective. Innovative design of catalysts for the...
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palladium The ligand L in the catalyst can be triphenylphosphine, dppe, BINAP, chiraphos or XPhos. Palladium catalysts in general have higher chemical...
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Corporation that is used in asymmetric synthesis. It was developed after BINAP and was investigated since it has a narrower dihedral angle between the...
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zirconium phosphonate-derived Ru-BINAP systems. Zirconium phosphonate-based chiral porous hybrid materials containing the Ru(BINAP)(diamine)Cl2 precatalysts...
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phosphines are C2-symmetric diphosphines. Famous examples are DIPAMP and BINAP. These chelating ligands support catalysts used in asymmetric hydrogenation...
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