Regio‐ and Stereoselective Iron‐Catalyzed Oxyazidation of Enamides Using a Hypervalent Iodine Reagent. Issue 70 (30th November 2017)

• Record Type: Journal Article
• Authors: Bertho, Sylvain; Rey‐Rodriguez, Romain; Colas, Cyril; Retailleau, Pascal; Gillaizeau, Isabelle
• Is Part Of: Chemistry. Volume 23:Issue 70(2017)
• Page Start: 17674
• Page End: 17677
• Publication Date: 2017-11-30
• Subjects: azides -- heterocycles -- hypervalent iodine -- iron catalysis -- radicals; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201704499
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A novel regio‐ and diastereoselective iron‐catalyzed intermolecular oxyazidation of enamides using various azidobenziodoxolone (ABX) derivatives is presented. A variety of α‐N3 amino derivatives and of α‐N3 piperidines were synthesized in good yields and under mild reaction conditions. The reaction involves a radical process using cheap FeCl2 as the initiator. Abstract : Iron catalysis : An iron‐catalyzed oxyazidation of enamides was developed. This provided an efficient route to α‐N3 amino derivatives and more specifically α‐N3 piperidine derivatives in good yields with high regio‐ and diastereoselectivity.