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Synthesis of Oxazolidin‐2‐ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water
Author(s) -
Buyck Thomas,
Pasche Delphine,
Wang Qian,
Zhu Jieping
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201505050
Subject(s) - chemistry , alkyl , double bond , group (periodic table) , medicinal chemistry , photochemistry , polymer chemistry , organic chemistry , combinatorial chemistry
Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs 2 CO 3 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.