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

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 am...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-09, Vol.138 (35), p.11353-11359
Main Authors: Momiyama, Norie, Tabuse, Hideaki, Noda, Hirofumi, Yamanaka, Masahiro, Fujinami, Takeshi, Yamanishi, Katsunori, Izumiseki, Atsuto, Funayama, Kosuke, Egawa, Fuyuki, Okada, Shino, Adachi, Hiroaki, Terada, Masahiro
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b07150