Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Lood, C.S.
dc.contributor.author Laine, A.E.
dc.contributor.author Högnäsbacka, A.
dc.contributor.author Nieger, M.
dc.contributor.author Koskinen, A.M.P
dc.date.accessioned 2016-09-16T09:39:01Z
dc.date.issued 2015
dc.identifier.citation Lood , C S , Laine , A E , Högnäsbacka , A , Nieger , M & Koskinen , A M P 2015 , ' Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group ' EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , vol 2015 , no. 17 , pp. 3793-3805 . DOI: 10.1002/ejoc.201500391 en
dc.identifier.issn 1434-193X
dc.identifier.other PURE UUID: 1eba6b46-0a11-47a3-ad93-df339e782f36
dc.identifier.other PURE ITEMURL: https://research.aalto.fi/en/publications/synthesis-of-chiral-2indolyl-methanamines-and-insight-into-the-stereochemistry-protecting-effects-of-the-9phenyl9fluorenyl-protecting-group(1eba6b46-0a11-47a3-ad93-df339e782f36).html
dc.identifier.other PURE FILEURL: https://research.aalto.fi/files/7173902/ms179_EJOC_2015_3793.pdf
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/21979
dc.description.abstract Tetrahydro-β-carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis of the structurally closely related compounds denoted as (indol-2-yl)methanamines, in 99% ee using amino acid starting materials, coupled with a 9-phenyl-9-fluorenyl (Pf) protecting group strategy. Furthermore a conformational study of Pfprotected α-amino carbonyl compounds were undertaken by means of DFT refined molecular mechanics calculation, Xray crystallography measurements and NMR experiments in order to elucidate the stereochemical protecting properties induced by the Pf group. en
dc.format.extent 3793-3805
dc.format.mimetype application/pdf
dc.language.iso en en
dc.relation.ispartofseries EUROPEAN JOURNAL OF ORGANIC CHEMISTRY en
dc.relation.ispartofseries Volume 2015, issue 17 en
dc.rights openAccess en
dc.subject.other 116 Chemical sciences en
dc.title Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group en
dc.type A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä fi
dc.description.version Peer reviewed en
dc.contributor.department School services, CHEM
dc.contributor.department Department of Chemistry en
dc.subject.keyword 116 Chemical sciences
dc.identifier.urn URN:NBN:fi:aalto-201609163861
dc.identifier.doi 10.1002/ejoc.201500391
dc.type.version acceptedVersion


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