ChemInform Abstract: Inverse-Electron-Demand Diels-Alder Reactions of Masked o-Benzoquinones with Enol Ethers and Styrene.

ChemInform ◽  
2001 ◽  
Vol 32 (19) ◽  
pp. no-no
Author(s):  
Shih-Yu Gao ◽  
San Ko ◽  
Yen-Lin Lin ◽  
Rama Krishna Peddinti ◽  
Chun-Chen Liao
Keyword(s):  
Diels Alder ◽  
Enol Ethers ◽  
Inverse Electron Demand ◽  
Electron Demand

The catalytic asymmetric synthesis of tetrahydropyridazines via inverse electron-demand aza-Diels–Alder reaction of enol ethers with azoalkenes

2015 ◽  
Vol 51 (84) ◽  
pp. 15374-15377 ◽  
Author(s):  
Liang Wei ◽  
Chun-Jiang Wang
Keyword(s):  
Asymmetric Synthesis ◽  
Good Yield ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enol Ethers ◽  
Inverse Electron Demand ◽  
Catalytic Asymmetric Synthesis ◽  
Diels Alder Reaction ◽  
Catalytic Asymmetric ◽  
Electron Demand

A highly efficient catalytic asymmetric IEDDA reaction of azoalkenes with enol ethers is reported. This methodology provides a facile entry to biologically important tetrahydropyridazines in good yield with good to excellent ee.

Inverse-electron-demand Diels–Alder reactions of masked o-benzoquinones with enol ethers and styrene

Tetrahedron ◽  
2001 ◽  
Vol 57 (2) ◽  
pp. 297-308 ◽  
Author(s):  
Shih-Yu Gao ◽  
San Ko ◽  
Yen-Lin Lin ◽  
Rama Krishna Peddinti ◽  
Chun-Chen Liao
Keyword(s):  
Diels Alder ◽  
Enol Ethers ◽  
Inverse Electron Demand ◽  
Electron Demand

Copper‐Catalyzed Enantioselective Inverse Electron‐Demand Hetero‐Diels–Alder Reactions of Diazadienes with Enol Ethers: Efficient Synthesis of Chiral Pyridazines

2013 ◽  
Vol 355 (18) ◽  
pp. 3539-3544 ◽  
Author(s):  
Shuang Gao ◽  
Jia‐Rong Chen ◽  
Xiao‐Qiang Hu ◽  
Hong‐Gang Cheng ◽  
Liang‐Qiu Lu ◽  
...  
Keyword(s):  
Diels Alder ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Inverse Electron Demand ◽  
Electron Demand

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

Synthese neuer Pyridin-C-nukleoside der 2 ,3 -Didesoxyribose durch „inverse“ [4+2]-Cycloaddition Synthesis of Novel Pyridine-C-nucleosides of 2,3-Dideoxyribose by „Inverse“ [4+2]-Cycloaddition

1997 ◽  
Vol 52 (7) ◽  
pp. 851-858 ◽  
Author(s):  
Gunther Seitz ◽  
Johanna Siegl
Keyword(s):  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Novel ◽  
Protecting Group ◽  
Enol Ethers ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Cyclic Ketene Acetals

The anomeric imido esters 5 and 6, appropriate precursors for C-nucleoside synthesis, were prepared and utilized as heterodienophiles in a Diels-Alder reaction with inverse electron demand to yield the novel, protected 1.2.4-triazine C-nucleosides 8 and 9. They could be deprotected by treatment with 70% trifluoroacetic acid to furnish the free C-nucleosides 10 and 11. The triazine „aglycon“ of 8 contains an electron deficient diazadiene system, highly activated to react with various electron rich dienophiles such as enamines, enol ethers and several cyclic ketene acetals in an „inverse“ [4+2]-cycloaddition reaction. The Diels-Alder adducts spontaneously eliminate N2 and after follow-up reactions the O-TBDPS protected pyridine-C-nucleosides 13, 15, 17,19, 21 and 23 are formed. Removal of the protecting group by treatment with CF3CO2H /H2O leads to the corresponding 2’,3’-dideoxy-β-D-ribofuranosyl- pyridines.

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