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DC Field | Value | Language |
---|---|---|
dc.citation.endPage | 3634 | - |
dc.citation.number | 22 | - |
dc.citation.startPage | 3629 | - |
dc.citation.title | ORGANIC & BIOMOLECULAR CHEMISTRY | - |
dc.citation.volume | 11 | - |
dc.contributor.author | Lee, Hogyu | - |
dc.contributor.author | Kim, Jun Hee | - |
dc.contributor.author | Lee, Won Koo | - |
dc.contributor.author | Cho, Jaeheung | - |
dc.contributor.author | Nam, Wonwoo | - |
dc.contributor.author | Lee, Jaedeok | - |
dc.contributor.author | Ha, Hyun-Joon | - |
dc.date.accessioned | 2023-12-22T03:43:43Z | - |
dc.date.available | 2023-12-22T03:43:43Z | - |
dc.date.created | 2020-09-03 | - |
dc.date.issued | 2013-06 | - |
dc.description.abstract | Polyhydroxylated pyrrolidines, such as biologically important azafuranoses represented by the natural product (+)-2,5-imino-2,5,6-trideoxy-gulo-heptitol and its C(3)-epimer, were elaborated from a commercially available enantiomerically pure (2R)-hydroxymethylaziridine by highly stereoselective directed reactions in more than 61% overall yield. At first, the nucleophile 2-trimethylsilyloxyfuran was directed to (2R)-aziridine-2-carboxaldehyde by ZnBr2 to yield the unusual anti-addition product as a single isomer via the chelation-controlled transition. The ring opening of aziridine was followed by conjugate addition to give a cis-fused bicycle, which was converted to the target molecule after the required reductive operations. | - |
dc.identifier.bibliographicCitation | ORGANIC & BIOMOLECULAR CHEMISTRY, v.11, no.22, pp.3629 - 3634 | - |
dc.identifier.doi | 10.1039/c3ob27390c | - |
dc.identifier.issn | 1477-0520 | - |
dc.identifier.scopusid | 2-s2.0-84877743511 | - |
dc.identifier.uri | https://scholarworks.unist.ac.kr/handle/201301/48131 | - |
dc.identifier.url | https://pubs.rsc.org/en/content/articlelanding/2013/OB/c3ob27390c#!divAbstract | - |
dc.identifier.wosid | 000318917000006 | - |
dc.language | 영어 | - |
dc.publisher | ROYAL SOC CHEMISTRY | - |
dc.title | Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine | - |
dc.type | Article | - |
dc.description.isOpenAccess | FALSE | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.type.docType | Article | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.subject.keywordPlus | GLYCOSIDASE INHIBITORS | - |
dc.subject.keywordPlus | VINYLOGOUS ALDOL | - |
dc.subject.keywordPlus | PYRROLIDINE | - |
dc.subject.keywordPlus | PIPERIDINE | - |
dc.subject.keywordPlus | REAGENTS | - |
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