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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A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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Date
2015
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Language
en
Pages
3793-3805
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Volume 2015, issue 17
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.
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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 . https://doi.org/10.1002/ejoc.201500391