title: An enantioselective Diels-Alder reaction of 1,2-dihydropyridines with α-acyloxyacroleins catalyzed by a chiral primary ammonium salt.
abstract: The first enantioselective Diels-Alder reaction of 1,2-dihydropyridines with α-acyloxyacroleins catalyzed by a chiral primary ammonium salt has been developed and it offers more efficient routes to key synthetic intermediates of alkaloids, for which the direct preparations were unavailable before. The asymmetric induction can be understood through the optimized geometry of an iminium salt aqua complex derived from the catalyst and the dienophile.
authors.affiliation: Graduate School of Engineering, Nagoya University, B2-3(611), Furo-cho, Chikusa, Nagoya 464-8603, Japan. ishihara@cc.nagoya-u.ac.jp.
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Ishihara
authors.forename: Hiroki
authors.initials: H
authors.lastname: Yamada
authors.forename: Matsujiro
authors.initials: M
authors.lastname: Akakura
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004095:Dihydropyridines / Q000737:chemistry*; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004095:Dihydropyridines; D000644:Quaternary Ammonium Compounds; D000171:Acrolein