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.
We describe herein the atroposelective formal synthesis of (–)‐steganone, a parent member of Steganotaenia araliacea dibenzocyclooctadiene lignan lactones. Our synthesis features an atropodiastereoselective biaryl Suzuki–Miyaura cross‐coupling reaction with de up to 99 % using as a chiral auxiliary an enantiopure and efficiently converted β‐hydroxy sulfoxide derivative.
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