Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

Marina Sicignano; Ricardo I. Rodríguez; Vito Capaccio; Fabio Borello; Rafael Cano; Francesco De Riccardis; Luca Bernardi; Sergio Díaz-Tendero; Giorgio Della Sala; José Alemán

doi:10.1039/D0OB00476F

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis†

Marina Sicignano,

^a Ricardo I. Rodríguez,

^b Vito Capaccio,

^b Fabio Borello,^a Rafael Cano,

^b Francesco De Riccardis,

^a Luca Bernardi,

^c Sergio Díaz-Tendero,

^d Giorgio Della Sala

*^a and José Alemán

*^b

Author affiliations

* Corresponding authors

^a Dipartimento di Chimica e Biologia “A. Zambelli”, Università degli Studi di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano, SA, Italy
E-mail: gdsala@unisa.it

^b Organic Chemistry Department, Módulo 1, Universidad Autónoma de Madrid, 28049 Madrid, Spain
E-mail: jose.aleman@uam.es

^c Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy

^d Chemistry Department, Módulo 13, Universidad Autónoma de Madrid, 28049 Madrid, Spain

Abstract

The first enantioselective method for the installation of the SCF₃ group at the C-4 position of azlactones is described in the present communication under quinidinium phase transfer catalysis. The higher performance of substrates containing electron-rich 2-aryl groups at the azlactone was rationalized using DFT calculations.

This article is part of the themed collection: Catalysis & biocatalysis in OBC

Organic & Biomolecular Chemistry

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

Social activity

Search articles by author

Spotlight

Advertisements