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Intramolecular Palladium-Catalyzed Aminocarboxylation of Olefins as a Direct Route to Bicyclic Oxazolidinones

โœ 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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โœฆ Synopsis


Abstract

An efficient, direct synthesis of oxazolidinones fused to sixโ€membered heterocyclic rings starting from carbamateโ€protected aminoalkenes has been developed. This procedure is based on an oxidative palladium(II)โ€catalyzed 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 palladiumโ€promoted transfer of the nitrogen atom on the C๏ฃพC double bond.


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