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

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

doi:10.1021/jacs.6b07150

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

Norie Momiyama, Hideaki Tabuse, Hirofumi Noda, Masahiro Yamanaka, Takeshi Fujinami, Katsunori Yamanishi, Atsuto Izumiseki, Kosuke Funayama, Fuyuki Egawa, Shino Okada, Hiroaki Adachi, Masahiro Terada

理学研究科・化学専攻

研究成果: Article › 査読

22 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	11353-11359
ページ数	7
ジャーナル	Journal of the American Chemical Society
巻	138
号	35
DOI	https://doi.org/10.1021/jacs.6b07150
出版ステータス	Published - 2016 9 7

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

文献へのアクセス

10.1021/jacs.6b07150

フィンガープリント「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」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

Momiyama, N., Tabuse, H., Noda, H., Yamanaka, M., Fujinami, T., Yamanishi, K., Izumiseki, A., Funayama, K., Egawa, F., Okada, S., Adachi, H., & Terada, M. (2016). 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. Journal of the American Chemical Society, 138(35), 11353-11359. https://doi.org/10.1021/jacs.6b07150

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. / Momiyama, Norie; Tabuse, Hideaki; Noda, Hirofumi; Yamanaka, Masahiro; Fujinami, Takeshi; Yamanishi, Katsunori; Izumiseki, Atsuto; Funayama, Kosuke; Egawa, Fuyuki; Okada, Shino; Adachi, Hiroaki; Terada, Masahiro.

In: Journal of the American Chemical Society, Vol. 138, No. 35, 07.09.2016, p. 11353-11359.

研究成果: Article › 査読

Momiyama, N, Tabuse, H, Noda, H, Yamanaka, M, Fujinami, T, Yamanishi, K, Izumiseki, A, Funayama, K, Egawa, F, Okada, S, Adachi, H & Terada, M 2016, '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', Journal of the American Chemical Society, vol. 138, no. 35, pp. 11353-11359. https://doi.org/10.1021/jacs.6b07150

Momiyama N, Tabuse H, Noda H, Yamanaka M, Fujinami T, Yamanishi K et al. 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. Journal of the American Chemical Society. 2016 9 7;138(35):11353-11359. https://doi.org/10.1021/jacs.6b07150

Momiyama, Norie ; Tabuse, Hideaki ; Noda, Hirofumi ; Yamanaka, Masahiro ; Fujinami, Takeshi ; Yamanishi, Katsunori ; Izumiseki, Atsuto ; Funayama, Kosuke ; Egawa, Fuyuki ; Okada, Shino ; Adachi, Hiroaki ; Terada, Masahiro. / 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. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 35. pp. 11353-11359.

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