DC Field | Value | Language |
---|---|---|
dc.contributor.author | Ajitha, Manjaly J. | ko |
dc.contributor.author | Suresh, Cherumuttathu H. | ko |
dc.date.accessioned | 2014-09-01T08:25:25Z | - |
dc.date.available | 2014-09-01T08:25:25Z | - |
dc.date.created | 2014-07-17 | - |
dc.date.created | 2014-07-17 | - |
dc.date.created | 2014-07-17 | - |
dc.date.issued | 2013-12 | - |
dc.identifier.citation | TETRAHEDRON LETTERS, v.54, no.52, pp.7144 - 7146 | - |
dc.identifier.issn | 0040-4039 | - |
dc.identifier.uri | http://hdl.handle.net/10203/189489 | - |
dc.description.abstract | The mechanism of the NHC-catalyzed intermolecular Stetter reaction between benzaldehyde and cyclopropene has been investigated using the PCM-M062X/6-311++G(3df,2p)//M062X/6-31+G(d,p) level of DFT. Compared to the direct reaction, a substantial reduction in the activation free energy by 10.6-14.4 kcal/mol is observed when the reaction is performed in the presence of water, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The bases promote the proton transfer step of the reaction to yield the Breslow intermediate. An early concerted transition state has been located for the stereocontrolling C-C bond formation step (Delta G(#) = 26.6 kcal/mol) which is used to explain the diastereomeric ratio observed in the experiment. | - |
dc.language | English | - |
dc.publisher | PERGAMON-ELSEVIER SCIENCE LTD | - |
dc.subject | GAMMA-BUTYROLACTONES | - |
dc.subject | NHC CATALYSIS | - |
dc.subject | HYDROACYLATION | - |
dc.subject | ALDEHYDES | - |
dc.subject | CYCLOPROPENES | - |
dc.subject | ANNULATIONS | - |
dc.subject | CHEMISTRY | - |
dc.subject | KINETICS | - |
dc.subject | UMPOLUNG | - |
dc.subject | STATES | - |
dc.title | Role of base assisted proton transfer in N-heterocyclic carbene-catalyzed intermolecular Stetter reaction | - |
dc.type | Article | - |
dc.identifier.wosid | 000327805800014 | - |
dc.identifier.scopusid | 2-s2.0-84888134754 | - |
dc.type.rims | ART | - |
dc.citation.volume | 54 | - |
dc.citation.issue | 52 | - |
dc.citation.beginningpage | 7144 | - |
dc.citation.endingpage | 7146 | - |
dc.citation.publicationname | TETRAHEDRON LETTERS | - |
dc.identifier.doi | 10.1016/j.tetlet.2013.10.116 | - |
dc.contributor.localauthor | Ajitha, Manjaly J. | - |
dc.contributor.nonIdAuthor | Suresh, Cherumuttathu H. | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | Organocatalysis | - |
dc.subject.keywordAuthor | N-Heterocyclic carbene | - |
dc.subject.keywordAuthor | Stetter reaction | - |
dc.subject.keywordAuthor | Breslow intermediate | - |
dc.subject.keywordAuthor | Density functional theory | - |
dc.subject.keywordPlus | GAMMA-BUTYROLACTONES | - |
dc.subject.keywordPlus | NHC CATALYSIS | - |
dc.subject.keywordPlus | HYDROACYLATION | - |
dc.subject.keywordPlus | ALDEHYDES | - |
dc.subject.keywordPlus | CYCLOPROPENES | - |
dc.subject.keywordPlus | ANNULATIONS | - |
dc.subject.keywordPlus | CHEMISTRY | - |
dc.subject.keywordPlus | KINETICS | - |
dc.subject.keywordPlus | UMPOLUNG | - |
dc.subject.keywordPlus | STATES | - |
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