Molecular Design of a Chiral Bronsted 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

作者：Momiyama Norie^*; Tabuse Hideaki; Noda Hirofumi; Yamanaka Masahiro; Fujinami Takeshi; Yamanishi Katsunori; Izumiseki Atsuto; Funayama Kosuke; Egawa Fuyuki; Okada Shino; Adachi Hiroaki; Terada Masahiro^*

来源：Journal of the American Chemical Society, 2016, 138(35): 11353-11359.

DOI：10.1021/jacs.6b07150

A chiral Bronsted acid containing two different acidic sites, chiral carboxylic acid monophosphoric acid la, was designed to be a new and effective concept in catalytic asymmetric hetero-Diels Alder reactions of azopyridine-carboxylate with amidodienes. The multipoint hydrogen bonding interactions among the carboxylic acid, mono phosphoric acid, azopyridinecarboxylate, and amidodiene achieved high catalytic and chiral efficiency, producing substituted 1,2,3,6-tetrahydropyridazines with excellent stereo control in a single step. This constitutes the first example of regio-, diastereo-, and enantioselective azo-hetero-Diels Alder reactions by chiral Bronsted acid catalysis.

• 出版日期2016-9-7