Catalytic Asymmetric Pictet–Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines

A new strategy has been introduced to develop a catalytic asymmetric Pictet–Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet–Spengler-type reaction with imines at room temperature...

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Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (20), p.5636-5639
Main Authors: Cheng, Dao-Juan, Wu, Hai-Bian, Tian, Shi-Kai
Format: Article
Language:English
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Summary:A new strategy has been introduced to develop a catalytic asymmetric Pictet–Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet–Spengler-type reaction with imines at room temperature to give structurally diverse indolo[3,4-cd][1]benzazepines in good to excellent yields and ee.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202361t