First efficient synthesis of SF5-substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides with pentafluorosulfanyl-substituted acrylic esters and amides

Ewelina Falkowska; Vincent Tognetti; Laurent Joubert; Philippe Jubault; Jean-Philippe Bouillon; Xavier Pannecoucke

doi:10.1039/C4RA14075C

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First efficient synthesis of SF₅-substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides with pentafluorosulfanyl-substituted acrylic esters and amides†

Ewelina Falkowska,^a Vincent Tognetti,^a Laurent Joubert,^a Philippe Jubault,*^a Jean-Philippe Bouillon*^a and Xavier Pannecoucke^a

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* Corresponding authors

^a Normandie Univ., COBRA, UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France
E-mail: jean-philippe.bouillon@univ-rouen.fr, philippe.jubault@insa-rouen.fr

Abstract

For the first time, di-, tri- and tetrasubstituted pentafluorosulfanylated pyrrolidines have been efficiently synthetized via 1,3-dipolar cycloaddition. In the case of tetra-substituted pyrrolidines, an unusual mixture of 1/1 regioisomers was obtained. Theoretical calculations have been carried out and the regioselectivity has been explained compared to the results previously obtained in the trifluoromethylated pyrrolidine series.

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Article information

DOI: https://doi.org/10.1039/C4RA14075C
Article type: Communication
Submitted: 07 Nov 2014
Accepted: 17 Dec 2014
First published: 17 Dec 2014

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RSC Adv., 2015,5, 6864-6868

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First efficient synthesis of SF₅-substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides with pentafluorosulfanyl-substituted acrylic esters and amides

E. Falkowska, V. Tognetti, L. Joubert, P. Jubault, J. Bouillon and X. Pannecoucke, RSC Adv., 2015, 5, 6864 DOI: 10.1039/C4RA14075C

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