Dual Gold‐Catalyzed Cycloaromatization of Unconjugated (E)‐Enediynes

A synthesis of unconjugated (E)‐enediynes from allenyl amino alcohols is reported and their gold‐catalyzed cascade cycloaromatization to a broad range of enantioenriched substituted isoindolinones has been developed. Experimental and computational studies support the reaction proceeding via a dual‐g...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-02, Vol.58 (7), p.2114-2119
Main Authors: Zamani, Farzad, Babaahmadi, Rasool, Yates, Brian F., Gardiner, Michael G., Ariafard, Alireza, Pyne, Stephen G., Hyland, Christopher J. T.
Format: Article
Language:English
Subjects:
Alcohols
Chemical synthesis
Computer applications
cycloaromatization
dual-gold catalysis
Enediynes
Gold
isoindolinones
Vinylidene
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Summary:A synthesis of unconjugated (E)‐enediynes from allenyl amino alcohols is reported and their gold‐catalyzed cascade cycloaromatization to a broad range of enantioenriched substituted isoindolinones has been developed. Experimental and computational studies support the reaction proceeding via a dual‐gold σ,π‐activation mode, involving a key gold‐vinylidene‐ and allenyl‐gold‐containing intermediate. Dual gold catalysis: A synthesis of unconjugated (E)‐enediynes from allenyl amino alcohols is reported and their gold‐catalyzed cascade cycloaromatization to a broad range of enantioenriched substituted isoindolinones has been developed.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201810794