N-Fluorenyltryptamines as a Useful Platform for Catalytic Enantio­selective Pictet–Spengler Reactions

Abstract

In the presence of a thiourea–carboxylic acid catalyst, N-9-fluorenyltryptamines undergo highly enantioselective Pictet–Spengler reactions with a range of aldehydes. The reaction works particularly well with aromatic aldehydes, tolerating electronically diverse substituents in all ring positions. Electron-deficient tryptamines are viable substrates. Removal of the fluorenyl protecting group is readily accomplished without deterioration of product ee.

Key words

Pictet–Spengler reaction - asymmetric catalysis - Brønsted acid catalysis - heterocycles - ion pairing

Publikationsverlauf

Eingereicht: 15. August 2022

Angenommen nach Revision: 31. Oktober 2022

Accepted Manuscript online:
31. Oktober 2022

Artikel online veröffentlicht:
05. Dezember 2022

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