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Asymmetric hydrogenation information


Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information (what chemists refer to as chirality) to transfer from one molecule to the target, forming the product as a single enantiomer. The chiral information is most commonly contained in a catalyst and, in this case, the information in a single molecule of catalyst may be transferred to many substrate molecules, amplifying the amount of chiral information present. Similar processes occur in nature, where a chiral molecule like an enzyme can catalyse the introduction of a chiral centre to give a product as a single enantiomer, such as amino acids, that a cell needs to function. By imitating this process, chemists can generate many novel synthetic molecules that interact with biological systems in specific ways, leading to new pharmaceutical agents and agrochemicals. The importance of asymmetric hydrogenation in both academia and industry contributed to two of its pioneers — William Standish Knowles and Ryōji Noyori — being collectively awarded one half of the 2001 Nobel Prize in Chemistry.[1]

  1. ^ "The Nobel Prize in Chemistry 2001". 2001-10-10.

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Asymmetric hydrogenation

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Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity...

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Transfer hydrogenation

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need for high-pressure molecular H2 used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions...

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Hydrogenation

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non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces double and triple bonds in hydrocarbons. Hydrogenation has three...

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Enantioselective synthesis

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catalysts are effective for only one type of asymmetric reaction. For example, Noyori asymmetric hydrogenation with BINAP/Ru requires a β-ketone, although...

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Kinetic resolution

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resolution of 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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Dynamic kinetic resolution in asymmetric synthesis

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products. One of the more classic applications of DKR is Noyori's asymmetric hydrogenation. The presence of an acidic center between two carbonyl groups allows...

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BINAP

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PMID 12914496. Zhang, Zhenfeng; Butt, Nicholas A.; Zhang, Wanbin (2016). "Asymmetric Hydrogenation of Nonaromatic Cyclic Substrates". Chemical Reviews. 116 (23):...

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Phosphinooxazolines

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for asymmetric hydrogenation. Iridium complexes incorporating phosphinooxazoline ligands have been shown to be effective for 'classic' hydrogenation using...

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William Standish Knowles

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prize with Ryōji Noyori for their work in asymmetric synthesis, specifically for his work in hydrogenation reactions. The other half was awarded to K...

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Rhodium

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measure the neutron flux level. Other uses of rhodium include asymmetric hydrogenation used to form drug precursors and the processes for the production...

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Diphenylethylenediamine

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precursor for catalysts for asymmetric transfer hydrogenation. For example, (cymene)Ru(S,S-TsDPEN) catalyzes the hydrogenation of benzil into (R,R)-hydrobenzoin...

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Phosphoramidite ligand

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autonomously described the use of phosphoramidite ligands for asymmetric hydrogenation. High enantioselectivities were reached, rivaling those using the...

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Tetrahydroquinoline

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prepared by hydrogenation of the corresponding quinoline using heterogeneous catalysts. Tetrahydroquinolines are produced by hydrogenation of quinolines...

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Iridium

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complexes are often active for asymmetric hydrogenation both by traditional hydrogenation. and transfer hydrogenation. This property is the basis of the...

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DuPhos

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was introduced in 1991 by M.J. Burk and first demonstrated in asymmetric hydrogenation of certain enamide esters to amino acid precursors: Other chiral...

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Sacubitril

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carboxylate by hydrolysis using lithium hydroxide in aqueous ethanol. Asymmetric hydrogenation using a ruthenium catalyst and a chiral bisphosphine ligand sets...

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Ruthenium

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awarded in 2001 to Ryōji Noyori for contributions to the field of asymmetric hydrogenation. Ruthenium-promoted cobalt catalysts are used in Fischer–Tropsch...

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Catalysis

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complexes, in Noyori asymmetric hydrogenation: One of the most obvious applications of catalysis is the hydrogenation (reaction with hydrogen gas) of fats using...

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Timeline of Monsanto

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names: authors list (link) Schuck, 1987: p. 17 William S. Knowles. ASYMMETRIC HYDROGENATIONS. Nobel Lecture, December 8, 2001 E. Fred Schubert (2003). "1"...

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Geraniol

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Shin-ichi; Tokunaga, Makoto; Kitamura, Masato; Noyori, Ryoji (1995). "Asymmetric Hydrogenation of Allylic Alcohols Using BINAP–Ruthenium Complexes: (S)-(−)-citronellol"...

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Monsanto

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team invented a way to selectively synthesize enantiomers via asymmetric hydrogenation. This was the first method for the catalytic production of pure...

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Chiral pool

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component of catalysts used for asymmetric hydrogenation: Diisopinocampheylborane is an organoborane that is useful for asymmetric synthesis of secondary alcohols...

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