Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 남원우 | * |
dc.date.accessioned | 2016-08-28T10:08:58Z | - |
dc.date.available | 2016-08-28T10:08:58Z | - |
dc.date.issued | 2013 | * |
dc.identifier.issn | 1477-0520 | * |
dc.identifier.other | OAK-10096 | * |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/223735 | - |
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. This journal is © The Royal Society of Chemistry 2013. | * |
dc.language | English | * |
dc.title | Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine | * |
dc.type | Article | * |
dc.relation.issue | 22 | * |
dc.relation.volume | 11 | * |
dc.relation.index | SCI | * |
dc.relation.index | SCIE | * |
dc.relation.index | SCOPUS | * |
dc.relation.startpage | 3629 | * |
dc.relation.lastpage | 3634 | * |
dc.relation.journaltitle | Organic and Biomolecular Chemistry | * |
dc.identifier.doi | 10.1039/c3ob27390c | * |
dc.identifier.wosid | WOS:000318917000006 | * |
dc.identifier.scopusid | 2-s2.0-84877743511 | * |
dc.author.google | Lee H. | * |
dc.author.google | Kim J.H. | * |
dc.author.google | Lee W.K. | * |
dc.author.google | Cho J. | * |
dc.author.google | Nam W. | * |
dc.author.google | Lee J. | * |
dc.author.google | Ha H.-J. | * |
dc.contributor.scopusid | 남원우(7006569723) | * |
dc.date.modifydate | 20240116111857 | * |