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organocatalysis wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 introduction 2 organocatalyst classes 3 proline 4 imidazolidinone organocatalysis 5 thiourea organocatalysis 6 references 7 external links toggle the table of contents organocatalysis 17 languages العربية čeština dansk deutsch ελληνικά español eesti فارسی suomi gaeilge italiano 日本語 português simple english slovenčina türkçe 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikiquote wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia redirected from organocatalytic method in organic chemistry justus von liebig s synthesis of oxamide from dicyan and water represents the first organocatalytic reaction with acetaldehyde further identified as the first discovered pure organocatalyst which act similarly to the then named ferments now known as enzymes 1 2 in organic chemistry organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst this organocatalyst consists of carbon hydrogen sulfur and other nonmetal elements found in organic compounds 3 4 5 6 7 8 because of their similarity in composition and description they are often mistaken as a misnomer for enzymes due to their comparable effects on reaction rates and forms of catalysis involved organocatalysts which display secondary amine functionality can be described as performing either enamine catalysis by forming catalytic quantities of an active enamine nucleophile or iminium catalysis by forming catalytic quantities of an activated iminium electrophile this mechanism is typical for covalent organocatalysis covalent binding of substrate normally requires high catalyst loading for proline catalysis typically 20 30 mol noncovalent interactions such as hydrogen bonding facilitates low catalyst loadings down to 0 001 mol organocatalysis offers several advantages there is no need for metal based catalysis thus making a contribution to green chemistry in this context simple organic acids have been used as catalyst for the modification of cellulose in water on multi ton scale 9 when the organocatalyst is chiral an avenue is opened to asymmetric catalysis for example the use of proline in aldol reactions is an example of chirality and green chemistry 10 organic chemists david macmillan and benjamin list were both awarded the 2021 nobel prize in chemistry for their work on asymmetric organocatalysis 11 introduction edit regular achiral organocatalysts are based on nitrogen such as piperidine used in the knoevenagel condensation 12 dmap used in esterifications 13 and dabco used in the baylis hillman reaction 14 thiazolium salts are employed in the stetter reaction 15 these catalysts and reactions have a long history but current interest in organocatalysis is focused on asymmetric catalysis with chiral catalysts called asymmetric organocatalysis or enantioselective organocatalysis a pioneering reaction developed in the 1970s is called the hajos parrish eder sauer wiechert reaction between 1968 and 1997 there were only a few reports of the use of small organic molecules as catalysts for asymmetric reactions the hajos parrish reaction probably being the most famous but these chemical studies were viewed more as unique chemical reactions than as integral parts of a larger interconnected field 16 in this reaction naturally occurring chiral proline is the chiral catalyst in an aldol reaction the starting material is an achiral triketone and it requires just 3 of proline to obtain the reaction product a ketol in 93 enantiomeric excess this is the first example of an amino acid catalyzed asymmetric aldol reaction 17 18 the asymmetric synthesis of the wieland miescher ketone 1985 is also based on proline and another early application was one of the transformations in the total synthesis of erythromycin by robert b woodward 1981 19 a mini review digest article focuses on selected recent examples of total synthesis of natural and pharmaceutical products using organocatalytic reactions 20 many chiral organocatalysts are an adaptation of chiral ligands which together with a metal center also catalyze asymmetric reactions and both concepts overlap to some degree a breakthrough in the field of organocatalysis came in 1997 when yian shi reported the first general highly enantioselective organocatalytic reaction with the catalytic asymmetric epoxidation of trans and trisubstituted olefins with chiral dioxiranes 21 since that time several different types of reactions have been developed organocatalyst classes edit organocatalysts for asymmetric synthesis can be grouped in several classes biomolecules proline phenylalanine secondary amines in general 22 the cinchona alkaloids certain oligopeptides synthetic catalysts derived from biomolecules hydrogen bonding catalysts including taddols derivatives of binol such as nobin and organocatalysts based on thioureas triazolium salts as next generation stetter reaction catalysts examples of asymmetric reactions involving organocatalysts are asymmetric diels alder reactions asymmetric michael reactions asymmetric mannich reactions shi epoxidation organocatalytic transfer hydrogenation proline edit main article proline organocatalysis proline catalysis has been reviewed 23 24 imidazolidinone organocatalysis edit imidazolidinone catalysts imidazolidinones are catalysts for many transformations such as asymmetric diels alder reactions and michael additions chiral catalysts induce asymmetric reactions often with high enantioselectivities this catalyst works by forming an iminium ion with carbonyl groups of α β unsaturated aldehydes enals and enones in a rapid chemical equilibrium this iminium activation is similar to activation of carbonyl groups by a lewis acid and both catalysts lower the substrate s lumo 25 26 the transient iminium intermediate is chiral which is transferred to the reaction product via chiral induction the catalysts have been used in diels alder reactions michael additions friedel crafts alkylations transfer hydrogenations and epoxidations one example is the asymmetric synthesis of the drug warfarin in equilibrium with the hemiketal in a michael addition of 4 hydroxycoumarin and benzylideneacetone 27 a recent exploit is the vinyl alkylation of crotonaldehyde with an organotrifluoroborate salt 28 for other examples of its use see organocatalytic transfer hydrogenation and asymmetric diels alder reactions thiourea organocatalysis edit main article thiourea organocatalysis a large group of organocatalysts incorporate the urea or the thiourea moiety these catalytically effective thio urea derivatives termed thio urea organocatalysts provide explicit double hydrogen bonding interactions to coordinate and activate h bond accepting substrates 29 their current uses are restricted to asymmetric multicomponent reactions including those involving michael addition asymmetric multicomponent reactions for the synthesis of spirocycles asymmetric multicomponent reactions involving acyl strecker reactions asymmetric petasis reactions asymmetric biginelli reactions asymmetric mannich reactions asymmetric aza henry reactions and asymmetric reductive coupling reactions 30 references edit justus von liebig justus 1860 ueber die bildung des oxamids aus cyan annalen der chemie und pharmacie 113 2 246 247 doi 10 1002 jlac 18601130213 w langenbeck 1929 über organische katalysatoren iii die bildung von oxamid aus dicyan bei gegenwart von aldehyden liebigs ann 469 16 25 doi 10 1002 jlac 19294690103 berkessel a groeger h 2005 asymmetric organocatalysis weinheim wiley vch isbn 978 3 527 30517 9 special issue list benjamin 2007 organocatalysis chem rev 107 12 5413 5883 doi 10 1021 cr078412e peter i dalko lionel moisan 2004 in the golden age of organocatalysis angew chem int ed 43 39 5138 5175 doi 10 1002 anie 200400650 pmid 15455437 matthew j gaunt carin c c johansson andy mcnally ngoc t vo 2007 enantioselective organocatalysis drug discovery today 12 1 2 8 27 doi 10 1016 j drudis 2006 11 004 pmid 17198969 dieter enders christoph grondal matthias r m hüttl 2007 asymmetric organocatalytic domino reactions angew chem int ed 46 10 1570 1581 doi 10 1002 anie 200603129 pmid 17225236 peter i dalko lionel moisan 2001 enantioselective organocatalysis angew chem int ed 40 20 3726 3748 doi 10 1002 1521 3773 20011015 40 20 3726 aid anie3726 3 0 co 2 d pmid 11668532 international patent wo 2006068611 a1 20060629 direct homogeneous and heterogeneous organic acid and amino acid catalyzed modification of amines and alcohols inventors armando córdova stockholm sweden jonas hafrén stockholm sweden example 4 in u s patent 3 975 440 august 17 1976 filed dec 9 1970 zoltan g hajos and david r parrish 2021 nobel prize in chemistry nobel prize retrieved 6 october 2021 list b 2010 emil knoevenagel and the roots of aminocatalysis angewandte chemie international edition in english 49 10 1730 1734 doi 10 1002 anie 200906900 pmid 20175175 neises bernhard steglich wolfgang july 1978 simple method for the esterification of carboxylic acids angewandte chemie international edition in english 17 7 522 524 doi 10 1002 anie 197805221 basavaiah deevi rao anumolu jaganmohan satyanarayana tummanapalli march 2003 recent advances in the baylis hillman reaction and applications chemical reviews 103 3 811 892 doi 10 1021 cr010043d pmid 12630854 stetter hermann 1976 catalyzed addition of aldehydes to activated double bonds a new synthetic approach angewandte chemie international edition in english 15 11 639 647 doi 10 1002 anie 197606391 issn 1521 3773 macmillan david w c 2008 the advent and development of organocatalysis nature 455 7211 springer science and business media llc 304 308 bibcode 2008natur 455 304m doi 10 1038 nature07367 issn 0028 0836 pmid 18800128 s2cid 205215034 z g hajos d r parrish german patent de 2102623 1971 zoltan g hajos david r parrish 1974 asymmetric synthesis of bicyclic intermediates of natural product chemistry j org chem 39 12 1615 1621 doi 10 1021 jo00925a003 r b woodward e logusch k p nambiar k sakan d e ward b w au yeung p balaram l j browne et al 1981 asymmetric total synthesis of erythromcin 1 synthesis of an erythronolide a secoacid derivative via asymmetric induction j am chem soc 103 11 3210 3213 bibcode 1981jachs 103 3210w doi 10 1021 ja00401a049 b f sun 2015 total synthesis of natural and pharmaceutical products powered by organocatalytic reactions tetrahedron lett 56 17 2133 2140 doi 10 1016 j tetlet 2015 03 046 wang zhi xian tu yong frohn michael zhang jian rong shi yian 1997 11 01 an efficient catalytic asymmetric epoxidation method journal of the american chemical society 119 46 11224 11235 bibcode 1997jachs 11911224w doi 10 1021 ja972272g issn 0002 7863 bertelsen søren 2009 organocatalysis after the gold rush chemical society reviews 38 8 2178 89 doi 10 1039 b903816g pmid 19623342 gaunt m j johansson c c c mcnally a vo n t 2007 enantioselective organocatalysis drug discovery today 12 1 2 8 27 doi 10 1016 j drudis 2006 11 004 pmid 17198969 kucherenko a s siyutkin d e maltsev o v kochetkov s v zlotin s g 2013 asymmetric organocatalysis from proline to highly efficient immobilized organocatalysts russian chemical bulletin 61 7 1313 doi 10 1007 s11172 012 0177 4 s2cid 93168492 gérald lelais david w c macmillan 2006 modern strategies in organic catalysis the advent and development of iminium activation pdf aldrichimica acta 39 3 79 erkkilä anniinä majander inkeri pihko petri m 2007 iminium catalysis chem rev 107 12 5416 5470 doi 10 1021 cr068388p pmid 18072802 nis halland tore hansen karl anker jørgensen 2003 organocatalytic asymmetric michael reaction of cyclic 1 3 dicarbonyl compounds and α β unsaturated ketones a highly atom economic catalytic one step formation of optically active warfarin anticoagulant angew chem int ed 42 40 4955 4957 doi 10 1002 anie 200352136 pmid 14579449 sandra lee david w c macmillan 2007 organocatalytic vinyl and friedel crafts alkylations with trifluoroborate salts pdf j am chem soc 129 50 15438 15439 doi 10 1021 ja0767480 pmid 18031044 s2cid 34848947 madarász ádám dósa zsolt varga szilárd soós tibor csámpai antal pápai imre july 2016 thiourea derivatives as brønsted acid organocatalysts pdf acs catalysis 6 7 4379 4387 doi 10 1021 acscatal 6b00618 parvin tasneem yadava rahul choudhury lokman 2020 recent applications of thiourea based organocatalysts in asymmetric multicomponent reactions amcrs org biomol chem 18 29 5513 5532 doi 10 1039 d0ob00595a pmid 32644077 external links edit scholia has a profile for organocatalysis q898995 media related to organocatalysis at wikimedia commons the dictionary definition of organocatalysis at wiktionary quotations related to organocatalysis at wikiquote v t e concepts in enantioselective synthesis chirality types chirality stereocenter planar chirality c 2 symmetric ligands axial chirality supramolecular chirality inherent chirality chiral molecules stereoisomer enantiomer diastereomer meso compound racemic mixture enantiomeric excess ee diastereomeric excess de analysis optical rotation chiral derivatizing agents nmr spectroscopy of stereoisomers ultraviolet visible spectroscopy of stereoisomers chiral resolution recrystallization kinetic resolution chiral column chromatography diastereomeric recrystallization reactions asymmetric induction chiral pool synthesis chiral auxiliaries asymmetric catalysis organocatalysis biocatalysis retrieved from https en wikipedia org w index php title organocatalysis oldid 1311511045 categories catalysis organic chemistry hidden categories articles with short description short description matches wikidata commons category link from wikidata this page was last edited on 15 september 2025 at 14 09 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents organocatalysis 17 languages add topic