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Molecules 2016, 21(6), 699; doi:10.3390/molecules21060699

The Chiral Pool in the Pictet–Spengler Reaction for the Synthesis of β-Carbolines

Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Arcavacata di Rende (Cs) 87030, Italy
Academic Editors: Carlo Siciliano and Constantinos Athanassopoulos
Received: 27 April 2016 / Revised: 18 May 2016 / Accepted: 24 May 2016 / Published: 27 May 2016
(This article belongs to the Special Issue Synthesis of Bioactive Compounds from the Chiral Pool)

Abstract

The Pictet–Spengler reaction (PSR) is the reaction of a β-arylethylamine with an aldehyde or ketone, followed by ring closure to give an aza-heterocycle. When the β-arylethylamine is tryptamine, the product is a β-carboline, a widespread skeleton in natural alkaloids. In the natural occurrence, these compounds are generally enantiopure, thus the asymmetric synthesis of these compounds have been attracting the interest of organic chemists. This review aims to give an overview of the asymmetric PSR, in which the chirality arises from optically pure amines or carbonyl compounds both from natural sources and from asymmetric syntheses to assemble the reaction partners. View Full-Text
Keywords: Pictet-Spengler reaction; asymmetric synthesis; β-carboline; alkaloids Pictet-Spengler reaction; asymmetric synthesis; β-carboline; alkaloids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Dalpozzo, R. The Chiral Pool in the Pictet–Spengler Reaction for the Synthesis of β-Carbolines. Molecules 2016, 21, 699.

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