TY - JOUR
T1 - Molecular Design of a Chiral Brønsted Acid with Two Different Acidic Sites
T2 - Regio-, Diastereo-, and Enantioselective Hetero-Diels-Alder Reaction of Azopyridinecarboxylate with Amidodienes Catalyzed by Chiral Carboxylic Acid-Monophosphoric Acid
AU - Momiyama, Norie
AU - Tabuse, Hideaki
AU - Noda, Hirofumi
AU - Yamanaka, Masahiro
AU - Fujinami, Takeshi
AU - Yamanishi, Katsunori
AU - Izumiseki, Atsuto
AU - Funayama, Kosuke
AU - Egawa, Fuyuki
AU - Okada, Shino
AU - Adachi, Hiroaki
AU - Terada, Masahiro
N1 - Funding Information:
Support was partially provided by IMS, JSPS via Grant-in-Aid for Scientific Research C (No. 23550114) for N.M., and Grantin- Aid for Scientific Research on Innovative Area Advanced Molecular Transformations by Organocatalysts from MEXT, Japan (No. 23105002 for M.T., No. 23105005 for M.Y.).
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/9/7
Y1 - 2016/9/7
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.6b07150
DO - 10.1021/jacs.6b07150
M3 - Article
AN - SCOPUS:84986200946
VL - 138
SP - 11353
EP - 11359
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 35
ER -