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Totally selective synthesis of enantiopure (3S,5S)and (3R,5R)-4-amino-3,5-dihydroxypiperidines from aminodiepoxides derived from serine

dc.contributor.authorConcellón Gracia, José Manuel 
dc.contributor.authorRivero Espejel, Ignacio Alfredo
dc.contributor.authorRodríguez Solla, Humberto 
dc.contributor.authorConcellón Fernández, María del Carmen 
dc.contributor.authorArtega Morales, Estibaly España
dc.contributor.authorGarcía-Granda, Santiago 
dc.contributor.authorDíaz Fernández, María del Rosario 
dc.date.accessioned2013-01-30T10:10:16Z
dc.date.available2013-01-30T10:10:16Z
dc.date.issued2008
dc.identifier.citationJournal of Organic Chemistry, 73(15), p. 6048-6051 (2008); doi:10.1021/jo801058cspa
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10651/8861
dc.description.abstractThe transformation of enantiopure (2R,4R)- and (2S,4S)-N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine, 1 and 2, into the corresponding enantiopure (3S,5S)- and (3R,5R)-3,5-dihydroxy-3-aminopiperidines, 3 and 4 respectively, is described. The opening of the two epoxide rings with a range of amines takes place with total regioselectivity and high yields, in the presence of LiClO4. A mechanism to explain this transformation is proposed.spa
dc.format.extentp. 6048-6051spa
dc.language.isoeng
dc.relation.ispartofJournal of Organic Chemistryspa
dc.rights(c) American Chemical Society
dc.sourceWOKspa
dc.titleTotally selective synthesis of enantiopure (3S,5S)and (3R,5R)-4-amino-3,5-dihydroxypiperidines from aminodiepoxides derived from serinespa
dc.typejournal article
dc.identifier.local48spa
dc.identifier.doi10.1021/jo801058c
dc.relation.publisherversionhttp://dx.doi.org/10.1021/jo801058cspa


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