Synthesis of tetrahydro--carbolines via isomerization of N-allyltryptamines: a metal-catalyzed variation on the PictetSpengler themeElectronic supplementary information (ESI) available: Experimental procedures, characterization data for all substrates and products. See DOI: 10.1039/c2cc17704h

An efficient and broadly applicable alternative to the classical PictetSpengler synthesis of tetrahydro--carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile. A metal...

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Hauptverfasser: Ascic, Erhad, Hansen, Casper L, Le Quement, Sebastian T, Nielsen, Thomas E
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient and broadly applicable alternative to the classical PictetSpengler synthesis of tetrahydro--carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile. A metal-catalyzed alternative to the classical PictetSpengler synthesis of tetrahydro--carbolines is presented. The method relies on isomerization of allylic amines to form reactive iminium intermediates which react with a tethered indole nucleophile.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc17704h