title: Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking.
abstract: Described herein is a highly enantioselective synthesis of fused piperidine and pyrrolidine derivatives with all-carbon stereogenic centers. The enantioselective reductive amination from C(s)-symmetric 1,3-dione derivatives proceeded in a highly stereoselective manner by taking advantage of the desymmetrization approach to afford fused heterocycles with contiguous stereogenic centers in good to excellent enantioselectivities (up to 98% ee).
authors.affiliation: Department of Chemistry, Faculty of Science Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan. takahiko.akiyama@gakushuin.ac.jp and Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakacho Koganei, Tokyo 184-8588, Japan.
authors.forename: Keiji
authors.initials: K
authors.lastname: Mori
authors.affiliation: Department of Chemistry, Faculty of Science Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan. takahiko.akiyama@gakushuin.ac.jp.
authors.forename: Ayaka
authors.initials: A
authors.lastname: Miyake
authors.affiliation: Department of Chemistry, Faculty of Science Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan. takahiko.akiyama@gakushuin.ac.jp.
authors.forename: Takahiko
authors.initials: T
authors.lastname: Akiyama
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D010756:Phosphoric Acids; D010880:Piperidines; D011759:Pyrrolidines; C030242:phosphoric acid