title: Triple role of phenylselenonyl group enabled a one-pot synthesis of 1,3-oxazinan-2-ones from α-isocyanoacetates, phenyl vinyl selenones, and water.
abstract: Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.
authors: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland.
authors: Thomas
authors: T
authors: Buyck
authors: Qian
authors: Q
authors: Wang
authors: Jieping
authors: J
authors: Zhu
mesh_terms: D000085:Acetates / Q000737:chemistry*; D001557:Benzenesulfonates / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic; D002929:Cinchona / Q000737:chemistry; D002930:Cinchona Alkaloids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D014867:Water / Q000737:chemistry*
chemical_list: D000085:Acetates; D001557:Benzenesulfonates; D002930:Cinchona Alkaloids; D016566:Organoselenium Compounds; D016877:Oxidants; D014867:Water; C029501:4-toluenesulfonic acid; C007170:cyanoacetic acid; D010100:Oxygen