Regio- and Enantioselective Synthesis of N-Allylindoles by Iridium-Catalyzed Allylic Amination/Transition-Metal-Catalyzed Cyclization Reactions

Regio‐ and enantioselective synthesis of N‐allylindoles was realized through an iridium‐catalyzed asymmetric allylic amination reaction with 2‐alkynylanilines and subsequent transition‐metal‐catalyzed cyclization reactions. The highly enantioenriched allylic amines prepared from Ir‐catalysis were tr...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-03, Vol.20 (11), p.3040-3044
Main Authors: Ye, Ke-Yin, Dai, Li-Xin, You, Shu-Li
Format: Article
Language:English
Subjects:
allylic substitution
Amines
asymmetric catalysis
Asymmetry
Catalysis
Catalysts
Chemistry
enantioselectivity
iridium
N-allylindole
Synthesis (chemistry)
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Summary:Regio‐ and enantioselective synthesis of N‐allylindoles was realized through an iridium‐catalyzed asymmetric allylic amination reaction with 2‐alkynylanilines and subsequent transition‐metal‐catalyzed cyclization reactions. The highly enantioenriched allylic amines prepared from Ir‐catalysis were treated with catalytic amount of NaAuCl4⋅2 H2O or PdCl2 providing various substituted N‐allylindoles in excellent yields and enantioselectivities. Regio‐ and enantioselective synthesis of N‐allylindoles was realized through an iridium‐catalyzed asymmetric allylic amination reaction with 2‐alkynylanilines and subsequent transition‐metal‐catalyzed cyclization reactions (see scheme). The highly enantioenriched allylic amines prepared from Ir catalysis were treated with catalytic amount of NaAuCl4⋅2 H2O or PdCl2 providing various substituted N‐allylindoles in excellent yields and enantioselectivities (dbcot=dibenzo[a,e]cyclooctatetraene).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201400026