title: Organocatalytic conjugate addition of malononitrile to conformationally restricted dienones.
abstract: Organocatalytic conjugate addition of malononitrile to conformationally restricted dienones has been studied. A series of chiral primary and tertiary amine catalysts were screened. A piperidine-based thiourea-tertiary amine was found to be the efficient catalyst. Chiral pyran derivatives were obtained in excellent yields and enantioselectivities via a cascade conjugate addition-intramolecular cyclization pathway. The reaction is remarkably different for the corresponding reaction of conformationally flexible dienones.
authors.affiliation: Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
authors.forename: Zhi-Peng
authors.initials: ZP
authors.lastname: Hu
authors.forename: Chun-Liang
authors.initials: CL
authors.lastname: Lou
authors.forename: Jin-Jia
authors.initials: JJ
authors.lastname: Wang
authors.forename: Chun-Xia
authors.initials: CX
authors.lastname: Chen
authors.forename: Ming
authors.initials: M
authors.lastname: Yan
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007659:Ketones; D009570:Nitriles; C000945:dicyanmethane