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

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

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.

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2012-04, Vol.48 (27), p.3345-3347
Hauptverfasser: Ascic, Erhad, Hansen, Casper L, Le Quement, Sebastian T, Nielsen, Thomas E
Format: Artikel
Sprache:eng
Schlagworte:
Allyl Compounds - chemical synthesis
Carbolines - chemical synthesis
Catalysis
Coordination Complexes
Cyclization
Indoles - chemistry
Isomerism
Molecular Structure
Tryptamines - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc17704h