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rauhut currier reaction 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 references toggle the table of contents rauhut currier reaction 3 languages čeština español português 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 wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction the rauhut currier reaction also called the vinylogous morita baylis hillman reaction 1 is an organic reaction describing in its original scope the dimerization or isomerization of electron deficient alkenes such as enones by action of an organophosphine of the type r 3 p 2 in a more general description the rc reaction is any coupling of one active alkene latent enolate to a second michael acceptor creating a new c c bond between the alpha position of one activated alkene and the beta position of a second alkene under the influence of a nucleophilic catalyst 3 the reaction mechanism is essentially that of the related and better known baylis hillman reaction dabco not phosphine carbonyl not enone but the rauhut currier reaction actually predates it by several years in comparison to the mbh reaction the rc reaction lacks substrate reactivity and regioselectivity the original 1963 reaction described the dimerization of the ethyl acrylate to the ethyl diester of 2 methylene glutaric acid with tributylphosphine in acetonitrile rauhut currier reaction this reaction was also found to work for acrylonitrile rc cross couplings are known but suffer from lack of selectivity amines such as dabco can also act as catalyst the reactivity is improved in intramolecular rc reactions for example in the isomerization of di enones to form cyclopentenes 4 intramolecular rauhut currier reaction a similar reaction by asymmetric synthesis organocatalyzed by a protected cysteine and potassium tert butoxide afforded a cyclohexene with 95 enantiomeric excess 5 enantioselective rauhut currier reaction in this reaction the phosphine is replaced by the thiol group of cysteine but the reaction is the same references edit frank scott a mergott dustin j roush william r 1 march 2002 the vinylogous intramolecular morita baylis hillman reaction synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts journal of the american chemical society 124 11 2404 2405 bibcode 2002jachs 124 2404f doi 10 1021 ja017123j issn 0002 7863 pmid 11890766 preparation of dialkyl 2 methylene glutamates rauhut m m currier h u s patent 3074999 1963 january 22 american cyanamid co 1963 u s patent 3 074 999 aroyan carrie e dermenci alpay miller scott j 23 may 2009 the rauhut currier reaction a history and its synthetic application tetrahedron 65 21 4069 4084 doi 10 1016 j tet 2009 02 066 issn 0040 4020 wang long cheng luis ana liza agapiou kyriacos jang hye young krische michael j 1 march 2002 organocatalytic michael cycloisomerization of bis enones the intramolecular rauhut currier reaction journal of the american chemical society 124 11 2402 2403 bibcode 2002jachs 124 2402w doi 10 1021 ja0121686 issn 0002 7863 pmid 11890765 aroyan carrie e miller scott j 1 january 2007 enantioselective rauhut currier reactions promoted by protected cysteine journal of the american chemical society 129 2 256 257 bibcode 2007jachs 129 256a doi 10 1021 ja067139f issn 0002 7863 pmid 17212388 retrieved from https en wikipedia org w index php title rauhut currier_reaction oldid 1297321892 categories carbon carbon bond forming reactions name reactions hidden categories articles with short description short description matches wikidata use dmy dates from april 2023 this page was last edited on 25 june 2025 at 13 07 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 rauhut currier reaction 3 languages add topic