Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 35, Pages 11353-11359Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07150
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Funding
- IMS
- JSPS [23550114]
- MEXT, Japan [23105002, 23105005]
- JST-ACCEL
- Grants-in-Aid for Scientific Research [23550114] Funding Source: KAKEN
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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.
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