title: Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water.
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.
authors.affiliation: Laboratory of Synthesis and Natural Products, école Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
authors.forename: Thomas
authors.initials: T
authors.lastname: Buyck
authors.affiliation: Laboratory of Synthesis and Natural Products, école Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
authors.forename: Delphine
authors.initials: D
authors.lastname: Pasche
authors.affiliation: Laboratory of Synthesis and Natural Products, école Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.affiliation: Laboratory of Synthesis and Natural Products, école Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland. Jieping.zhu@epfl.ch.
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D002384:Catalysis; D009570:Nitriles / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D058451:Oxidative Coupling; D018036:Selenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D009570:Nitriles; D023303:Oxazolidinones; D018036:Selenium Compounds; D014753:Vinyl Compounds; D014867:Water
keywords: annulation; domino reactions; isocyanide; oxazolidinone; selenium