Fluoride Ion and Phosphines as Nucleophilic Catalysts: Synthesis of 1,4-Benzothiazepines from Cyclic Sulfenamides

Fluoride Ion and Phosphines as Nucleophilic Catalysts: Synthesis of 1,4-Benzothiazepines from Cyclic Sulfenamides

A new methodology, using fluoride ion as a nucleophilic catalyst, was applied for the synthesis of enantiopure 1,4-benzothiazepine from cyclic sulfenamide and electron-deficient acetylene, with high efficiency and atom economy.

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Veröffentlicht in:Journal of organic chemistry 2009-05, Vol.74 (10), p.3936-3939
Hauptverfasser: Spitz, Cédric, Lohier, Jean-François, Santos, Jana Sopkova-de Oliveira, Reboul, Vincent, Metzner, Patrick
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:A new methodology, using fluoride ion as a nucleophilic catalyst, was applied for the synthesis of enantiopure 1,4-benzothiazepine from cyclic sulfenamide and electron-deficient acetylene, with high efficiency and atom economy.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900449a