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

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

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 diastereoselectivi...

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Veröffentlicht in:Organic & biomolecular chemistry 2019-06, Vol.17 (25), p.6143-6147
Hauptverfasser: Ghisu, Lorenza, Melis, Nicola, Serusi, Lorenzo, Luridiana, Alberto, Soddu, Francesco, Secci, Francesco, Caboni, Pierluigi, Guillot, Régis, Aitken, David J, Frongia, Angelo
Format: Artikel
Sprache:eng
Schlagworte:
Amides
Carboxylic acids
Cascade chemical reactions
Crystallography
Cyclobutane
Derivatives
Information processing
Migration
Stereoselectivity
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Beschreibung
Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob00758j