title: Molecular Design of a Chiral Brønsted Acid with Two Different Acidic Sites: Regio-, Diastereo-, and Enantioselective Hetero-Diels-Alder Reaction of Azopyridinecarboxylate with Amidodienes Catalyzed by Chiral Carboxylic Acid-Monophosphoric Acid.
abstract: A chiral Brønsted acid containing two different acidic sites, chiral carboxylic acid-monophosphoric acid 1a, was designed to be a new and effective concept in catalytic asymmetric hetero-Diels-Alder reactions of azopyridinecarboxylate with amidodienes. The multipoint hydrogen-bonding interactions among the carboxylic acid, monophosphoric acid, azopyridinecarboxylate, and amidodiene achieved high catalytic and chiral efficiency, producing substituted 1,2,3,6-tetrahydropyridazines with excellent stereocontrol in a single step. This constitutes the first example of regio-, diastereo-, and enantioselective azo-hetero-Diels-Alder reactions by chiral Brønsted acid catalysis.
authors.affiliation: Institute for Molecular Science, Okazaki, Aichi 444-8787, Japan.|SOKENDAI (The Graduate University for Advanced Studies) , Okazaki, Aichi 444-8787, Japan.
authors.forename: Norie
authors.initials: N
authors.lastname: Momiyama
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Tabuse
authors.affiliation: Department of Chemistry, Faculty of Science, Rikkyo University , Toshima-ku, Tokyo, 171-8501, Japan.
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Noda
authors.affiliation: Department of Chemistry, Faculty of Science, Rikkyo University , Toshima-ku, Tokyo, 171-8501, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yamanaka
authors.affiliation: Institute for Molecular Science, Okazaki, Aichi 444-8787, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Fujinami
authors.affiliation: Institute for Molecular Science, Okazaki, Aichi 444-8787, Japan.
authors.forename: Katsunori
authors.initials: K
authors.lastname: Yamanishi
authors.affiliation: Institute for Molecular Science, Okazaki, Aichi 444-8787, Japan.|SOKENDAI (The Graduate University for Advanced Studies) , Okazaki, Aichi 444-8787, Japan.
authors.forename: Atsuto
authors.initials: A
authors.lastname: Izumiseki
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.|Graduate Research on Cooperative Education Program of IMS with Tohoku University , Okazaki, Aichi 444-8787, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Funayama
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Fuyuki
authors.initials: F
authors.lastname: Egawa
authors.affiliation: SOSHO, Inc., 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Shino
authors.initials: S
authors.lastname: Okada
authors.affiliation: SOSHO, Inc., 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Adachi
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.|Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Terada