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- Q7296135 subject Q7458901.
- Q7296135 subject Q8343673.
- Q7296135 abstract "The Rauhut–Currier reaction, also called the vinylogous Morita–Baylis–Hillman reaction, 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 R3P. 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. 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 reaction selectivity. The original 1963 reaction described the dimerization of the ethyl acrylate to the ethyl diester of 2-methylene-glutaric acid with tributylphosphine in acetonitrile: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:A similar reaction by asymmetric synthesis organocatalyzed by a protected cysteine and potassium tert-butoxide afforded a cyclohexene with 95% enantiomeric excess:In this reaction the phosphine is replaced by the thiol group of cysteine but the reaction is the same.".
- Q7296135 thumbnail Rauhut-Currier_reaction.png?width=300.
- Q7296135 wikiPageWikiLink Q1821552.
- Q7296135 wikiPageWikiLink Q186474.
- Q7296135 wikiPageWikiLink Q2182492.
- Q7296135 wikiPageWikiLink Q220410.
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- Q7296135 wikiPageWikiLink Q342968.
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- Q7296135 wikiPageWikiLink Q408047.
- Q7296135 wikiPageWikiLink Q408053.
- Q7296135 wikiPageWikiLink Q409622.
- Q7296135 wikiPageWikiLink Q413328.
- Q7296135 wikiPageWikiLink Q415233.
- Q7296135 wikiPageWikiLink Q423673.
- Q7296135 wikiPageWikiLink Q531306.
- Q7296135 wikiPageWikiLink Q568761.
- Q7296135 wikiPageWikiLink Q642233.
- Q7296135 wikiPageWikiLink Q648191.
- Q7296135 wikiPageWikiLink Q7458901.
- Q7296135 wikiPageWikiLink Q745930.
- Q7296135 wikiPageWikiLink Q7485453.
- Q7296135 wikiPageWikiLink Q7840573.
- Q7296135 wikiPageWikiLink Q812563.
- Q7296135 wikiPageWikiLink Q81406.
- Q7296135 wikiPageWikiLink Q82264.
- Q7296135 wikiPageWikiLink Q8343673.
- Q7296135 wikiPageWikiLink Q898525.
- Q7296135 wikiPageWikiLink Q898628.
- Q7296135 wikiPageWikiLink Q898995.
- Q7296135 wikiPageWikiLink Q903420.
- Q7296135 wikiPageWikiLink Q958860.
- Q7296135 comment "The Rauhut–Currier reaction, also called the vinylogous Morita–Baylis–Hillman reaction, 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 R3P.".
- Q7296135 label "Rauhut–Currier reaction".
- Q7296135 depiction Rauhut-Currier_reaction.png.