A practical and highly enantio- (up
to 94:6 er) and diastereoselective
(up to >20:1 dr) synthesis of γ-butenolides bearing two adjacent
stereogenic centers is reported featuring a sequential direct palladium-catalyzed
asymmetric allylic alkylation/(E)-selective cross-metathesis/[3,3]-sigmatropic
Cope rearrangement from readily available α-substituted (5H)-furan-2-ones.
We report here a highly selective copper(II)-catalysed asymmetric Friedel–Crafts conjugate addition/enantioselective protonation, which owes to a careful positioning of a bipyridine ligand within a DNA framework.
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.
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