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research article
Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water
Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2CO3 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.
Type
research article
Web of Science ID
WOS:000369855000013
Authors
Publication date
2016
Publisher
Published in
Volume
22
Issue
7
Start page
2278
End page
2281
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
February 16, 2016
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