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First asymmetric organocatalyzed domino Friedel–Crafts/lactonization reaction in the enantioselective synthesis of the GABABreceptor modulator (S)-BHFF
Journal article   Peer reviewed

First asymmetric organocatalyzed domino Friedel–Crafts/lactonization reaction in the enantioselective synthesis of the GABABreceptor modulator (S)-BHFF

Fabrizio Vetica, Renata Marcia de Figueiredo, Emilia Cupioli, Augusto Gambacorta, M. Antonietta Loretto, Martina Miceli and Tecla Gasperi
Tetrahedron Letters, (57), pp.750-753
07/01/2016
DOI: https://doi.org/10.1016/j.tetlet.2016.01.015

Abstract

Asymmetric organocatalysis Domino reaction PAMs Quaternary stereocenter 3H-Benzofuran-2-ones
An asymmetric domino Friedel–Crafts/lactonization sequence between phenols and trifluoropyruvatehas been accomplished for the first enantioselective synthesis of (S)-BHFF, a positive allosteric modulator(PAM) of GABAB receptor. The developed protocol leads to 3-OH-benzofuranone derivatives bearing aquaternary stereogenic center, and gives a valuable access to bioactive compounds with promising pharmaceuticalapplications
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