65899-49-2Relevant academic research and scientific papers
Diastereoselective synthesis of a highly substituted cis-decahydroquinoline via a Knoevenagel condensation
Huang, Junfeng,Bergmeier, Stephen C.
, p. 6434 - 6439 (2008)
A diastereoselective approach to 3,7,8-trisubstituted cis-decahydroquinolines is described. This ring system forms the core of rings B and E of the norditerpenoid alkaloid methyllycaconitine. This approach starts with a known disubstituted cyclohexene. The remaining carbons are attached via a Knoevenagel condensation followed by an intramolecular lactam formation. The stereochemistry of the substituents is controlled by the cis-substitution of the starting cyclohexene ring.
Chiral Pyridinium Phosphoramide as a Dual Br?nsted Acid Catalyst for Enantioselective Diels-Alder Reaction
Nishikawa, Yasuhiro,Nakano, Saki,Tahira, Yuu,Terazawa, Kanako,Yamazaki, Ken,Kitamura, Chitoshi,Hara, Osamu
supporting information, p. 2004 - 2007 (2016/06/01)
Chiral pyridinium phosphoramide 1·HX was designed to be a new class of chiral Br?nsted acid catalyst in which both the pyridinium proton and the adjacent imide-like proton activated by the electron-withdrawing pyridinium moiety could work cooperatively as strong dual proton donors. The potential of 1·HX was shown in the enantioselective Diels-Alder reactions of 1-amino dienes with various dienophiles including N-unsubstituted maleimide, which has yet to be successfully used in an asymmetric Diels-Alder reaction.
Molecular Design of a Chiral Br?nsted 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
supporting information, p. 11353 - 11359 (2016/10/12)
A chiral Br?nsted 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 Br?nsted acid catalysis.
