Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction

2017 ◽  
Vol 4 (5) ◽  
pp. 871-875 ◽  
Author(s):  
Longcheng Hong ◽  
Sebastian Ahles ◽  
Marcel A. Strauss ◽  
Christian Logemann ◽  
Hermann A. Wegner
Keyword(s):  
Lewis Acid ◽  
Acid Catalysis ◽  
Diels Alder ◽  
Lewis Acid Catalysis ◽  
Inverse Electron Demand ◽  
New Synthesis ◽  
Electron Demand

A new synthesis of aza-anthraquinones and substituted anthraquinones via bidentate Lewis acid catalysis has been developed.

Asymmetric Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis

Synlett ◽  
2021 ◽  
Author(s):  
Quan Cai ◽  
Xu-Ge Si ◽  
Zhi-Mao Zhang
Keyword(s):  
Lewis Acid ◽  
Acid Catalysis ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Natural Product Synthesis ◽  
Lewis Acid Catalysis ◽  
Reaction Conditions ◽  
Inverse Electron Demand ◽  
Bicyclic Lactones ◽  
Electron Demand

AbstractDiels–Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels–Alder reactions with Lewis acid catalysis are reviewed.1 Introduction2 State of the Art of Enantioselective Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis3 Enantioselective Synthesis of Arene cis-Dihydrodiols by Diels–­Alder/Retro-Diels–Alder Reactions of 2-Pyrones4 Enantioselective Synthesis of cis-Decalin Derivatives by Diels–­Alder Reactions of 2-Pyrones5 Conclusions

Cycloaddition Reactions of the Methano[10]annulene Derivative 9,9-Dichloro-1,4-dihydro-4a,8a-methanonaphthalene

1991 ◽  
Vol 44 (4) ◽  
pp. 555 ◽  
Author(s):  
B Halton ◽  
SGG Russell
Keyword(s):  
Maleic Anhydride ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Lewis Acid Catalysis ◽  
Inverse Electron Demand ◽  
Hydrophilic Solvent ◽  
Electron Demand

9,9-Dichloro-1,4-dihydro-4a,8a-methanonaphthalene (4) adds the electron-deficient dienophiles 4-phenyl-1,2,4-triazoline-3,5-dione, maleic anhydride and dimethyl acetylenedicarboxylate to the α-face to give adducts (5)-(7) respectively; the addition of the alkyne requires Lewis acid catalysis. Inverse electron-demand addition of 3,6-diphenyl-1,2,4,5-tetrazine to the monoene component of (4) in hydrophilic solvent (ethane-1,2-diol) is thwarted; the CCl2 bridge is ejected and the 1,4-dihydronaphthalene formed is captured to give (ultimately) phthalazine (16). Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate adds to (4) to give the methanobenzophthalazine (17b).

ChemInform Abstract: Control of Hetero-Diels-Alder Stereoselectivity Through Solvent Polarity and Broensted or Lewis Acid Catalysis; Theory and Experiment.

ChemInform ◽  
2014 ◽  
Vol 45 (12) ◽  
pp. no-no
Author(s):  
Olivier Loiseleur ◽  
Jerome Cassayre ◽  
Dominique Leca ◽  
Francesca Gaggini ◽  
Susan N. Pieniazek ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Acid Catalysis ◽  
Solvent Polarity ◽  
Diels Alder ◽  
Lewis Acid Catalysis ◽  
Theory And Experiment
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