doi: 10.1002/chem.201505050.
Epub 2016 Jan 8.
Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water
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- PMID: 26683868
- DOI: 10.1002/chem.201505050
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Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water
Chemistry.
.
Abstract
Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2 CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a single operation with the isocyano group acting formally as a polarized double bond and phenyl vinyl selenone as a latent 1,3-dipole. The phenylselenonyl group played a triple role as an electron-withdrawing group to activate the 1,4-addition, a leaving group, and a latent oxidant in this transformation.
Keywords: annulation; domino reactions; isocyanide; oxazolidinone; selenium.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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