Issue 7, 2016

Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding

Abstract

An Ir-catalyzed asymmetric synthesis of five-membered aza-spiroindolenines is achieved. Based on the detailed investigation of the reaction patterns of the aryl iminium migration, a one-pot asymmetric allylic dearomatization/migration sequence from racemic indole derivatives is realized, affording enantioenriched Pictet–Spengler-type products bearing an additional allylic stereogenic center adjacent to the C3 position of the indole core.

Graphical abstract: Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding

Supplementary files

Article information

Article type
Edge Article
Submitted
14 janv. 2016
Accepted
29 mars 2016
First published
29 mars 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 4453-4459

Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding

Q. Wu, C. Zheng, C. Zhuo and S. You, Chem. Sci., 2016, 7, 4453 DOI: 10.1039/C6SC00176A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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