Issue 12, 2019

Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres

Abstract

The first organocatalysed, metal-free cross-nucleophile coupling of indoles with α-branched aldehydes forming acyclic stereoselective quaternary carbon centres is presented. Applying an amino acid-derived catalyst with suitable organic oxidants affords the desired enantioenriched indole functionalised products with moderate to excellent yield and enantioselectivity. Two metal-free oxidative protocols employing either DDQ or a sequential approach that uses two organocatalysts to facilitate the use of O2 as the terminal oxidant are disclosed. These methods are compatible with various indoles ranging from electron-rich to -deficient substituents at the C-2, -5, -6, and -7-positions reacting with a series of different α-branched aldehydes.

Graphical abstract: Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres

Supplementary files

Article information

Article type
Edge Article
Submitted
13 jan 2019
Accepted
12 feb 2019
First published
13 feb 2019
This article is Open Access

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

Chem. Sci., 2019,10, 3586-3591

Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres

Nomaan M. Rezayee, V. H. Lauridsen, L. Næsborg, T. V. Q. Nguyen, H. N. Tobiesen and K. A. Jørgensen, Chem. Sci., 2019, 10, 3586 DOI: 10.1039/C9SC00196D

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