Synthesis of β-sulfinyl cyclobutane carboxylic amides via a formal α to β sulphoxide migration process

Lorenza Ghisu; Nicola Melis; Lorenzo Serusi; Alberto Luridiana; Francesco Soddu; Francesco Secci; Pierluigi Caboni; Régis Guillot; David J. Aitken; Angelo Frongia

doi:10.1039/C9OB00758J

Synthesis of β-sulfinyl cyclobutane carboxylic amides via a formal α to β sulphoxide migration process†

Lorenza Ghisu,^a Nicola Melis,^a Lorenzo Serusi,^a Alberto Luridiana,^a Francesco Soddu,^a Francesco Secci,

^a Pierluigi Caboni,^b Régis Guillot,

^c David J. Aitken

^c and Angelo Frongia

*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, I-09042, Monserrato, Cagliari, Italy
E-mail: afrongia@unica.it
Fax: +39-070-675-4388
Tel: +39-070-675-4406

^b Dipartimento di Scienze della Vita e dell'Ambiente, Università degli Studi di Cagliari, Via Ospedale 72, Cagliari, Italy

^c CP3A Organic Synthesis Group and Services Communs, ICMMO – CNRS UMR 8182, Université Paris Sud, Université Paris Saclay, 15 rue Georges Clemenceau, 91405 Orsay cedex, France

Abstract

An original tandem reaction consisting of a thermal elimination–addition process was developed. Highly substituted β-sulfinyl cyclobutane carboxylic acid derivatives were obtained from isomeric α-sulfinyl derivatives in a single operation in good to high yields and with high trans diastereoselectivity.

This article is part of the themed collection: Synthetic methodology in OBC

Organic & Biomolecular Chemistry

Synthesis of β-sulfinyl cyclobutane carboxylic amides via a formal α to β sulphoxide migration process†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Synthesis of β-sulfinyl cyclobutane carboxylic amides via a formal α to β sulphoxide migration process

Social activity

Search articles by author

Spotlight

Advertisements