Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: a metal-catalyzed variation on the Pictet–Spengler theme

Erhad Ascic, Casper L. Hansen, Sebastian T. Le Quement, Thomas Eiland Nielsen

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Abstract

An efficient and broadly applicable alternative to the classical Pictet–Spengler synthesis of tetrahydro-β-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.
Original languageEnglish
JournalChemical Communications
Volume48
Issue number27
Pages (from-to)3345-3347
ISSN1359-7345
DOIs
Publication statusPublished - 2012

Bibliographical note

Electronic supplementary information (ESI) available: Experimental procedures, characterization data for all substrates and products. See DOI: 10.1039/c2cc17704h

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