title: Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters.
abstract: Novel guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety.
authors.affiliation: Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588 Tokyo, Japan. odagi@cc.tuat.ac.jp.
authors.forename: Minami
authors.initials: M
authors.lastname: Odagi
authors.affiliation: Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588 Tokyo, Japan. k-takayama@koeichem.co.jp.
authors.forename: Kan
authors.initials: K
authors.lastname: Takayama
authors.affiliation: Department of Chemistry, Faculty of Science, Rikkyo University, 3-34-1, Nishi-Ikebukuro, Toshima-ku, 171-8501 Tokyo, Japan. msato_chem@rikkyo.ac.jp.
authors.forename: Makoto
authors.initials: M
authors.lastname: Sato
authors.affiliation: Department of Chemistry, Faculty of Science, Rikkyo University, 3-34-1, Nishi-Ikebukuro, Toshima-ku, 171-8501 Tokyo, Japan. myamanak@rikkyo.ac.jp.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yamanaka
authors.affiliation: Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588 Tokyo, Japan. knaga@cc.tuat.ac.jp.
authors.forename: Kazuo
authors.initials: K
authors.lastname: Nagasawa
mesh_terms: D002384:Catalysis; D006146:Guanidines / Q000737:chemistry*; D006900:Hydroxylation; D011759:Pyrrolidines / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D044024:Tetralones / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives*
chemical_list: D006146:Guanidines; D011759:Pyrrolidines; D044024:Tetralones; D014508:Urea
keywords: guanidine; organocatalyst; urea; α-hydroxylation