Asymmetric synthesis of bicyclic dihydropyrans via organocatalytic inverse-electron-demand oxo-Diels–Alder reactions of enolizable aliphatic aldehydes

2016 ◽  
Vol 52 (70) ◽  
pp. 10617-10620 ◽  
Author(s):  
Jun-Long Li ◽  
Kai-Chuan Yang ◽  
Yi Li ◽  
Qiang Li ◽  
Hong-Ping Zhu ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Diels Alder ◽  
Aliphatic Aldehydes ◽  
Inverse Electron Demand ◽  
Cyclic Enones ◽  
Electron Demand

An unprecedented highly enantioselective amine catalyzed oxo-IEDDA reaction of cyclic enones with enolizable aldehydes including aqueous acetaldehyde has been developed.

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.

Organocatalytic asymmetric synthesis of tetrahydrocarbazoles via an inverse-electron-demand Diels–Alder reaction of 2,3-indole-dienes with enals

2018 ◽  
Vol 5 (23) ◽  
pp. 3430-3434 ◽  
Author(s):  
Bo-Qi Gu ◽  
Wu-Lin Yang ◽  
Shu-Xiao Wu ◽  
Yan-Bing Wang ◽  
Wei-Ping Deng
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

A novel 2,3-indole-diene synthon was designed and first applied to an inverse-electron-demand Diels–Alder reaction to construct tetrahydrocarbazoles with excellent stereoselectivities.

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>

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