A general method for the synthesis of enantiopure 1,5-amino alcohols

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dc.contributor.authorGuignard, Guillaume Michel Pablo
dc.contributor.authorLlor Brunés, Núria
dc.contributor.authorUrbina Teixidor, Aina
dc.contributor.authorBosch Cartes, Joan
dc.contributor.authorAmat Tusón, Mercedes
dc.date.accessioned2016-05-27T16:03:53Z
dc.date.available2017-03-01T23:01:19Z
dc.date.issued2016-02
dc.date.updated2016-05-27T16:03:58Z
dc.description.abstractA variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the phenylethanol moiety gave enantiopure 5-amino-1-pentanols bearing substituents at the 2-, 3-, 4-, 2,2-, 2,3- 2,4- and 3,4-positions (28-36), which were isolated as their N-Boc derivatives.
dc.format.extent11 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec659329
dc.identifier.issn1434-193X
dc.identifier.urihttps://hdl.handle.net/2445/98971
dc.language.isoeng
dc.publisherWiley-VCH
dc.relation.isformatofVersió postprint del document publicat a: http://dx.doi.org/10.1002/ejoc.201501409
dc.relation.ispartofEuropean Journal of Organic Chemistry, 2016, vol. 2016, num. 4, p. 693-703
dc.relation.urihttp://dx.doi.org/10.1002/ejoc.201501409
dc.rights(c) Wiley-VCH, 2016
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
dc.subject.classificationSíntesi orgànica
dc.subject.classificationSíntesi asimètrica
dc.subject.classificationReducció química
dc.subject.classificationLactames
dc.subject.otherOrganic synthesis
dc.subject.otherAsymmetric synthesis
dc.subject.otherReduction (Chemistry)
dc.subject.otherLactams
dc.titleA general method for the synthesis of enantiopure 1,5-amino alcohols
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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