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Synthesis 2017; 49(24): 5387-5395
DOI: 10.1055/s-0036-1589104
DOI: 10.1055/s-0036-1589104
paper
An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines
This work was supported by grants from University of Camerino (Fondo di Ateneo per la Ricerca 2014-2015).Further Information
Publication History
Received: 13 July 2017
Accepted after revision: 09 August 2017
Publication Date:
07 September 2017 (online)
Abstract
An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through Lewis acid activated Povarov reaction is described. The protocol takes advantage of the very cheap, easy to handle, and environmentally friendly cerium trichloride as catalyst and allows to obtain either the anti- or the syn-isomer of the final tetrahydroquinoline with good selectivity, by performing the reaction in solvent or solventless conditions. The scope of the reaction is expanded to the one-pot synthesis of N-alkyltetrahydroquinolines through a very efficient iminium-Povarov approach. A deeper insight on the reaction system was provided by the study on the side reactions occurring in the reaction conditions and on the nature of the stereoselectivity.
Key words
tetrahydroquinoline derivatives - Povarov reaction - Lewis acid catalysis - cerium - solventless reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589104.
- Supporting Information
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Selected reviews on the Povarov reaction:
For recent reviews on this argument, see:
For some selected examples, see: