The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

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Abstract

The multicomponent Povarov reaction represents a powerful approach for the construction of substances containing N-heterocyclic frameworks. By using the Povarov reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines in a single step, it is possible to form the following new bonds: two Csp 3–Csp 3 and one Csp 3–Nsp 3, two Csp 2–Csp 2 and one Csp 2–Nsp 2, and four Csp 3–Csp 3 and two Csp 3–Nsp 1, respectively. This short review discusses the main features of the Povarov reaction, including its mechanism, the reaction scope by employing different catalysts and substrates, as well as stereoselective versions.

1 Introduction

2 Mechanism of the Povarov Reaction

3 Tetrahydroquinolines

4 Quinolines

5 Julolidines

6 Concluding Remarks

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Advances in the chemistry of tetrahydroquinolines.

Vellaisamy Sridharan, Padmakar A Suryavanshi, J Carlos Menéndez (2011)

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Asymmetric cooperative catalysis of strong Brønsted acid-promoted reactions using chiral ureas.

Hao Xu, Stephan Zuend, Matthew Woll … (2010)

Cationic organic intermediates participate in a wide variety of useful synthetic transformations, but their high reactivity can render selectivity in competing pathways difficult to control. Here, we describe a strategy for inducing enantioselectivity in reactions of protio-iminium ions, wherein a chiral catalyst interacts with the highly reactive intermediate through a network of noncovalent interactions. This interaction leads to an attenuation of the reactivity of the iminium ion and allows high enantioselectivity in cycloadditions with electron-rich alkenes (the Povarov reaction). A detailed experimental and computational analysis of this catalyst system has revealed the precise nature of the catalyst-substrate interactions and the likely basis for enantioinduction.