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.


Published in:
Chemistry - A European Journal, 22, 7, 2278-2281
Year:
2016
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
0947-6539
Keywords:
Laboratories:




 Record created 2016-02-16, last modified 2018-03-17


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