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Gold(I)‐Catalyzed Carboaminations of Allenes by N ‐Allyltetrahydro‐β‐carbolines: An Experimental and Theoretical Study
Author(s) -
Gobé Valérian,
Dousset Maxime,
Retailleau Pascal,
Gandon Vincent,
Guinchard Xavier
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601075
Subject(s) - chemistry , allene , isomerization , moiety , catalysis , density functional theory , photochemistry , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry
N ‐Allyltetrahydro‐β‐carbolines bearing a pendant allene undergo unprecedented gold(I)‐catalyzed cyclizations proceeding with an allyl migration from the nitrogen to the allene moiety. The initial product of the gold‐catalyzed cyclization evolves either via isomerization or Cope rearrangement, leading to different scaffolds. Density function theory (DFT) calculations established that the allyl migration occurs in an asynchronous suprafacial manner.