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

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The first organocatalysed, metal-free cross-nucleophile coupling of indoles with -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 O-2 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 -branched aldehydes.

OriginalsprogEngelsk
TidsskriftChemical Science
Vol/bind10
Nummer12
Sider (fra-til)3586-3591
Antal sider6
ISSN2041-6520
DOI
StatusUdgivet - mar. 2019

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