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DC Field | Value | Language |
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dc.citation.endPage | 6064 | - |
dc.citation.number | 45 | - |
dc.citation.startPage | 6054 | - |
dc.citation.title | CHEMICAL COMMUNICATIONS | - |
dc.citation.volume | 53 | - |
dc.contributor.author | Choi, Subin | - |
dc.contributor.author | Ha, Sujin | - |
dc.contributor.author | Park, Cheol-Min | - |
dc.date.accessioned | 2023-12-21T22:11:56Z | - |
dc.date.available | 2023-12-21T22:11:56Z | - |
dc.date.created | 2017-05-24 | - |
dc.date.issued | 2017-06 | - |
dc.description.abstract | This Feature Article introduces the preparation and synthetic utility of α-diazo oxime ethers. α-Oximino carbenes are useful synthons for N-heterocycles, and can be easily prepared from α-diazo oxime ethers as precursors. We begin with the preparation of α-diazo oxime ethers and their application in [3+2] cycloaddition. It turns out that the nature of metals bound to carbenes plays a crucial role in modulating the reactivity of α-oximino carbenes, in which copper carbenes smoothly react with enamines, whereas the less reactive enol ethers and nitriles require gold carbenes. In Section 3.2, a discussion on N-O and C-H bond activation is presented. Carbenes derived from diazo oxime ethers show unique reactivity towards N-O and C-H bond activation, in which the proximity of the two functionalities, carbene and oxime ether, dictates the preferred reaction pathways toward pyridines, pyrroles, and 2H-azirines. In Section 3.3, the development of tandem reactions based on α-diazo oxime ethers is discussed. The nature of carbenes in which whether free carbenes or metal complexes are involved dissects the pathway and forms different types of 2H-azirines. The 2H-azirine formation turned out to be an excellent platform for the tandem synthesis of N-heterocycles including pyrroles and pyridines. In the last section, we describe the electrophilic activation of 2H-azirines with vinyl carbenes and oximino carbenes. The resulting azirinium species undergo rapid ring expansion rearrangements to form pyridines and pyrazines. | - |
dc.identifier.bibliographicCitation | CHEMICAL COMMUNICATIONS, v.53, no.45, pp.6054 - 6064 | - |
dc.identifier.doi | 10.1039/C7CC02650A | - |
dc.identifier.issn | 1359-7345 | - |
dc.identifier.scopusid | 2-s2.0-85021726597 | - |
dc.identifier.uri | https://scholarworks.unist.ac.kr/handle/201301/21987 | - |
dc.identifier.url | http://pubs.rsc.org/en/Content/ArticleLanding/2017/CC/C7CC02650A#!divAbstract | - |
dc.identifier.wosid | 000402569200001 | - |
dc.language | 영어 | - |
dc.publisher | ROYAL SOC CHEMISTRY | - |
dc.title | alpha-Diazo oxime ethers for N-heterocycle synthesis | - |
dc.type | Article | - |
dc.description.isOpenAccess | FALSE | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.subject.keywordPlus | ONE-POT SYNTHESIS | - |
dc.subject.keywordPlus | C-H BONDS | - |
dc.subject.keywordPlus | RHODIUM(II) AZAVINYL CARBENES | - |
dc.subject.keywordPlus | HIGHLY SUBSTITUTED PYRROLES | - |
dc.subject.keywordPlus | RETRO-BUCHNER REACTION | - |
dc.subject.keywordPlus | DIAZOCARBONYL COMPOUNDS | - |
dc.subject.keywordPlus | TERMINAL ALKYNES | - |
dc.subject.keywordPlus | RING-EXPANSION | - |
dc.subject.keywordPlus | CYCLOADDITION REACTIONS | - |
dc.subject.keywordPlus | INSERTION REACTIONS | - |
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