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DC Field | Value | Language |
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dc.citation.endPage | 3202 | - |
dc.citation.number | 17 | - |
dc.citation.startPage | 3196 | - |
dc.citation.title | ADVANCED SYNTHESIS & CATALYSIS | - |
dc.citation.volume | 353 | - |
dc.contributor.author | Bae, Han Yong | - |
dc.contributor.author | Some, Surajit | - |
dc.contributor.author | Lee, Jae Heon | - |
dc.contributor.author | Kim, Ju-Young | - |
dc.contributor.author | Song, Myoung Jong | - |
dc.contributor.author | Lee, Sungyul | - |
dc.contributor.author | Zhang, Yong Jian | - |
dc.contributor.author | Song, Choong Eui | - |
dc.date.accessioned | 2023-12-22T05:38:43Z | - |
dc.date.available | 2023-12-22T05:38:43Z | - |
dc.date.created | 2019-02-11 | - |
dc.date.issued | 2011-12 | - |
dc.description.abstract | Highly enantioselective biomimetic Michael addition reactions of malonic acid half thioesters (MAHTs) to a variety of nitroolefins, affording the optically active gamma-amino acid precursors, were developed by employing the Cinchona-based squaramides (up to > 99% ee). Remarkably, this biomimetic process is enantioconvergent, a highly desirable feature of a catalytic asymmetric reaction, whereby E/Z-isomers of the nitroolefins afford the same product enantiomer. The synthetic utility of this organocatalytic protocol was also demonstrated in the formal synthesis of pharmaceutically important gamma-amino acids such as baclofen. Moreover, a quantum chemical analysis of the catalyst-substrate complexes is shown to give a detailed and instrumental insight into the origin of the observed catalytic activity. | - |
dc.identifier.bibliographicCitation | ADVANCED SYNTHESIS & CATALYSIS, v.353, no.17, pp.3196 - 3202 | - |
dc.identifier.doi | 10.1002/adsc.201100458 | - |
dc.identifier.issn | 1615-4150 | - |
dc.identifier.scopusid | 2-s2.0-82055163073 | - |
dc.identifier.uri | https://scholarworks.unist.ac.kr/handle/201301/25860 | - |
dc.identifier.url | https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201100458 | - |
dc.identifier.wosid | 000298171500019 | - |
dc.language | 영어 | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.title | Organocatalytic Enantioselective Michael-Addition of Malonic Acid Half-Thioesters to beta-Nitroolefins: From Mimicry of Polyketide Synthases to Scalable Synthesis of gamma-Amino Acids | - |
dc.type | Article | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.subject.keywordAuthor | gamma-amino acids | - |
dc.subject.keywordAuthor | biomimetic catalysis | - |
dc.subject.keywordAuthor | Cinchona-based squaramide catalysts | - |
dc.subject.keywordAuthor | malonic acid half thioesters (MAHTs) | - |
dc.subject.keywordAuthor | Michael addition | - |
dc.subject.keywordAuthor | organocatalysis | - |
dc.subject.keywordPlus | CONJUGATE ADDITION | - |
dc.subject.keywordPlus | ALDOL REACTIONS | - |
dc.subject.keywordPlus | ALPHA,BETA-UNSATURATED ALDEHYDES | - |
dc.subject.keywordPlus | BIFUNCTIONAL ORGANOCATALYSTS | - |
dc.subject.keywordPlus | STEREOSELECTIVE-SYNTHESIS | - |
dc.subject.keywordPlus | SQUARAMIDE DERIVATIVES | - |
dc.subject.keywordPlus | CHIRAL SQUARAMIDES | - |
dc.subject.keywordPlus | FATTY-ACID | - |
dc.subject.keywordPlus | CATALYST | - |
dc.subject.keywordPlus | BIOSYNTHESIS | - |
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