Intramolecular Palladium-Catalyzed Aminocarboxylation of Olefins as a Direct Route to Bicyclic Oxazolidinones
โ Scribed by Elena Borsini; Gianluigi Broggini; Andrea Fasana; Simona Galli; Maisaa Khansaa; Umberto Piarulli; Micol Rigamonti
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 293 KB
- Volume
- 353
- Category
- Article
- ISSN
- 1615-4150
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โฆ Synopsis
Abstract
An efficient, direct synthesis of oxazolidinones fused to sixโmembered heterocyclic rings starting from carbamateโprotected aminoalkenes has been developed. This procedure is based on an oxidative palladium(II)โcatalyzed reaction performed in the presence of stoichiometric copper chloride, which is determinant to promote the formation of the bicyclic product and prevent the isolation of the monocyclic amination product. Oxazolidinone compounds arise from a domino aminocarboxylation process through the direct intervention of the carbamate oxygen after the initial palladiumโpromoted transfer of the nitrogen atom on the C๏ฃพC double bond.
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