Synthesis 2017; 49(24): 5387-5395
DOI: 10.1055/s-0036-1589104
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines­

Cristina Cimarelli*a, Samuele Bordia, Pamela Piermatteia, Maura Pelleia, Fabio Del Bellob, Enrico Marcantonia
  • aSchool of Science and Technology - Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy   Email: cristina.cimarelli@unicam.it
  • bSchool of Pharmacy - Medicinal Chemistry Unit, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy
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 (eFirst)

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.

Supporting Information

 
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