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Access to Functionalized Imidazolidin‐2‐one Derivatives by Iron‐Catalyzed Oxyamination of Alkenes
Author(s) -
Manick AnneDoriane,
Aubert Sidonie,
Yalcouye Boubacar,
Prangé Thierry,
Berhal Farouk,
Prestat Guillaume
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802190
Subject(s) - alkene , aziridine , hydroxylamine , chemistry , catalysis , combinatorial chemistry , alcohol , double bond , organic chemistry , ring (chemistry)
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.