Access to Functionalized Imidazolidin‐2‐one Derivatives by Iron‐Catalyzed Oxyamination of Alkenes. Issue 44 (9th July 2018)

• Record Type: Journal Article
• Authors: Manick, Anne‐Doriane; Aubert, Sidonie; Yalcouye, Boubacar; Prangé, Thierry; Berhal, Farouk; Prestat, Guillaume
• Is Part Of: Chemistry. Volume 24:Issue 44(2018)
• Page Start: 11485
• Page End: 11492
• Publication Date: 2018-07-09
• Subjects: alkenes -- atom economy -- iron -- nitrogen heterocycles -- oxyamination; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201802190
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Functionalized imidazolidin‐2‐one were prepared by using an iron‐catalyzed alkene oxyamination reaction. Hydroxylamine derivatives were used in this atom‐economical process, and the addition of an external oxidant was not required. The conditions developed were shown to be efficient for mono‐, di‐, and trisubstituted double bonds, and a large scope of diamino alcohol precursors were delivered in good yields with good diastereoselectivities. The mechanistic pathway was studied and appears to involve both a fused aziridine and a carbocationic species. Abstract : Isn't it iron‐ic? The iron‐catalyzed intramolecular oxyamination of allylbenzoyloxy urea derivatives is described. This atom‐economical process uses hydroxylamine derivatives without the addition of any external oxidant and affords functionalized imidazolidin‐2‐one products as potential 2, 3‐diamino alcohol precursors. Mechanistic studies highlight the corresponding fused aziridine as a viable intermediate to explain this transformation.