Molecular Design of a Chiral Brønsted 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

2016 ◽  
Vol 138 (35) ◽  
pp. 11353-11359 ◽  
Author(s):  
Norie Momiyama ◽  
Hideaki Tabuse ◽  
Hirofumi Noda ◽  
Masahiro Yamanaka ◽  
Takeshi Fujinami ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Molecular Design ◽  
Alder Reaction ◽  
Diels Alder ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diels Alder Reaction ◽  
Brönsted Acid ◽  
Acidic Sites ◽  
Chiral Bronsted Acid

scholarly journals Asymmetric Brønsted acid-catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene

2012 ◽  
Vol 8 ◽  
pp. 1819-1824 ◽  
Author(s):  
Magnus Rueping ◽  
Sadiya Raja
Keyword(s):  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Reaction Conditions ◽  
Diels Alder Reaction ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

A new chiral Brønsted acid-catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene has been developed. The reaction provides optically active aza-tetracycles in good yields with high diastereo- and enantioselectivities under mild reaction conditions.

Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines

Synthesis ◽  
2021 ◽  
Author(s):  
Fabian Hofmann ◽  
Cornelius Gärtner ◽  
Martin Kretzschmar ◽  
Christoph Schneider
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Single Step ◽  
Diels Alder ◽  
Quinone Methide ◽  
Bronsted Acid ◽  
Atom Economy ◽  
Diels Alder Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

Aza-Diels Alder reactions are straightforward processes in the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid-bound ortho-quinone methide imines generating a range of interesting fused tetrahydro-quinolines in a diastereo- and enantioselective manner.

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