title: Asymmetric direct vinylogous Michael addition to 2-enoylpyridine N-oxides catalyzed by bifunctional thio-urea.
abstract: Catalytic enantioselective direct vinylogous Michael addition of α,α-dicyanoalkenes to 2-enoylpyridine N-oxides with a bifunctional organocatalyst is described. The methodology offers an efficient way to install an asymmetric carbon-carbon bond at the γ-position of α,α-dicyanoalkenes in excellent regio-, diastereo-, and enantioselectivity. Further, application in desymmetrization of achiral α,α-dicyanoalkene to access highly functionalized enantioenriched cyclohexylidenemalononitrile derivatives has been demonstrated.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal - 462 066, MP, India.
authors.forename: Subhrajit
authors.initials: S
authors.lastname: Rout
authors.forename: Sumit K
authors.initials: SK
authors.lastname: Ray
authors.forename: Rajshekhar A
authors.initials: RA
authors.lastname: Unhale
authors.forename: Vinod K
authors.initials: VK
authors.lastname: Singh
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D009570:Nitriles; D011725:Pyridines; C013229:pyridine N-oxide; C000945:dicyanmethane; D013890:Thiourea