Organocatalytic enantioselective synthesis of β-amino sulfonic acid derivatives

Emmanuel Deau; Alexandra Le Foll; Clémence Fouache; Emilie Corrot; Laetitia Bailly; Vincent Levacher; Pierric Marchand; Florian Querniard; Laurent Bischoff; Jean-François Brière

doi:10.1039/D1CC03477D

Organocatalytic enantioselective synthesis of β-amino sulfonic acid derivatives†

Emmanuel Deau,^a Alexandra Le Foll,

^a Clémence Fouache,^a Emilie Corrot,^a Laetitia Bailly,‡^a Vincent Levacher,^a Pierric Marchand,^b Florian Querniard,^b Laurent Bischoff*^a and Jean-François Brière

*^a

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* Corresponding authors

^a Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, Rouen 76000, France
E-mail: jean-francois.briere@insa-rouen.fr, laurent.bischoff@univ-rouen.fr
Web: http://www.lab-cobra.fr/equipes/heterocycles/

^b Holodiag, Voie de l’Innovation, Pharmaparc 2, Val de Reuil 27100, France

Abstract

An unprecedented enantioselective conjugate addition reaction of sodium bisulfite to various nitrostyrenes occurred upon the influence of a bifunctional amino-thiourea organocatalyst; a strategy that opens a straightforward route to unprotected chiral taurine derivatives thanks to the reduction of the obtained β-nitroethanesulfonic acids into the corresponding amino derivatives.

Chemical Communications

Organocatalytic enantioselective synthesis of β-amino sulfonic acid derivatives†

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Organocatalytic enantioselective synthesis of β-amino sulfonic acid derivatives

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