Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates

The highly efficient synthesis of the enantioenriched spiroindolines by iridium‐catalyzed asymmetric allylic dearomatization and reduction is presented. Spiroindolines containing three contiguous stereogenic centers were obtained with excellent diastereo‐ and enantioselectivity. In addition, a chira...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-11, Vol.54 (47), p.14146-14149
Main Authors: Zhuo, Chun-Xiang, Zhou, Yong, Cheng, Qiang, Huang, Lin, You, Shu-Li
Format: Article
Language:English
Subjects:
asymmetric catalysis
dearomatization
heterocycles
iridium
synthetic methods
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Summary:The highly efficient synthesis of the enantioenriched spiroindolines by iridium‐catalyzed asymmetric allylic dearomatization and reduction is presented. Spiroindolines containing three contiguous stereogenic centers were obtained with excellent diastereo‐ and enantioselectivity. In addition, a chiral tryptamine derivative could be easily accessed in good yield with excellent ee value through an unprecedented dearomatization/retro‐Mannich/hydrolysis cascade reaction of an indole derivative. On a tryp: The highly efficient synthesis of enantioenriched spiroindolines by an iridium‐catalyzed asymmetric allylic dearomatization and reduction has been realized. The spiroindolines contain three contiguous chiral centers and are obtained with excellent diastereo‐ and enantioselectivities. Furthermore, a chiral tryptamine derivative could also be accessed with excellent enantioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201507193