Multistep One-Pot Synthesis of Enantioenriched Polysubstituted Cyclopenta[b]indoles

Simple steps, complex result: Consecutive organo‐catalyzed reactions of 3‐indolylmethanol compounds with aldehydes and N‐protected indoles lead to the formation of structurally complex cyclopenta[b]indoles (see scheme, Bn=benzyl). These one‐pot multistep reactions have a broad substrate scope and gi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-01, Vol.51 (4), p.1059-1062
Main Authors: Xu, Biao, Guo, Zhi-Lei, Jin, Wan-Yan, Wang, Zhi-Ping, Peng, Yun-Gui, Guo, Qi-Xiang
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
alkylations
Catalysis
Cyclopentanes - chemistry
indoles
Indoles - chemical synthesis
Indoles - chemistry
multistep reactions
one-pot syntheses
organocatalysis
Stereoisomerism
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Summary:Simple steps, complex result: Consecutive organo‐catalyzed reactions of 3‐indolylmethanol compounds with aldehydes and N‐protected indoles lead to the formation of structurally complex cyclopenta[b]indoles (see scheme, Bn=benzyl). These one‐pot multistep reactions have a broad substrate scope and give the products in high yields, and with excellent diastereoselectivities and enantioselectivities.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201107308