2016年9月
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
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- 巻
- 138
- 号
- 35
- 開始ページ
- 11353
- 終了ページ
- 11359
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/jacs.6b07150
- 出版者・発行元
- AMER CHEMICAL SOC
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.
- リンク情報
- ID情報
-
- DOI : 10.1021/jacs.6b07150
- ISSN : 0002-7863
- Web of Science ID : WOS:000382901800048