Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxy-piperidines - development of a phosphite-driven cyclodehydration

dc.contributorAalto-yliopistofi
dc.contributorAalto Universityen
dc.contributor.authorHuy, Peter H.
dc.contributor.authorWestphal, Julia C.
dc.contributor.authorKoskinen, Ari M.P.
dc.contributor.departmentDepartment of Chemistryen
dc.date.accessioned2016-09-16T08:25:36Z
dc.date.issued2014
dc.description.abstractA concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.en
dc.description.versionPeer revieweden
dc.format.extent369-383
dc.format.mimetypeapplication/pdf
dc.identifier.citationHuy , P H , Westphal , J C & Koskinen , A M P 2014 , ' Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxy-piperidines - development of a phosphite-driven cyclodehydration ' , Beilstein Journal of Organic Chemistry , vol. 10 , no. 10 , pp. 369-383 . https://doi.org/10.3762/bjoc.10.35en
dc.identifier.doi10.3762/bjoc.10.35
dc.identifier.issn1860-5397
dc.identifier.otherPURE UUID: 843f521d-bb3d-47fe-b854-46b9603d6881
dc.identifier.otherPURE ITEMURL: https://research.aalto.fi/en/publications/843f521d-bb3d-47fe-b854-46b9603d6881
dc.identifier.otherPURE FILEURL: https://research.aalto.fi/files/7157122/ms171_BJOC_2014_369.pdf
dc.identifier.urihttps://aaltodoc.aalto.fi/handle/123456789/21964
dc.identifier.urnURN:NBN:fi:aalto-201609163845
dc.language.isoenen
dc.relation.ispartofseriesBEILSTEIN JOURNAL OF ORGANIC CHEMISTRYen
dc.relation.ispartofseriesVolume 10, issue 10en
dc.rightsopenAccessen
dc.titleConcise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxy-piperidines - development of a phosphite-driven cyclodehydrationen
dc.typeA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessäfi
dc.type.versionpublishedVersion
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