First efficient synthesis of SF5-substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides with pentafluorosulfanyl-substituted acrylic esters and amides†,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,Vincent Tognetti,Laurent Joubert,Philippe Jubault,Jean-Philippe Bouillon,Xavier Pannecoucke

RSC Advances Pub Date : 12/17/2014 00:00:00 , DOI:10.1039/C4RA14075C

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.