Hydrogen-Bonding Catalysis of Tetraalkylammonium Salts in an Aza-Diels-Alder Reaction.
A piperidine-derived tetraalkylammonium salt with a non-coordinating counteranion worked as an effective hydrogen-bonding catalyst in an aza-Diels-Alder reaction of imines and a Danishefsky diene. The hydrogen-bonding interaction between the ammonium salt and an imine was observed as part of a (1) H NMR titration study.
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Yusuke
Y
Kumatabara
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Shiho
S
Kaneko
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Satoshi
S
Nakata
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. seijishirakawa@nagasaki-u.ac.jp.
Seiji
http://orcid.org/0000-0003-1027-8922
S
Shirakawa
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan.
Keiji
K
Maruoka
aza-Diels-Alder reaction; hydrogen bonds; hydrogen-bonding catalysis; organocatalysis; tetraalkylammonium salts