scholarly journals Unconventional exo selectivity in thermal normal-electron-demand Diels–Alder reactions

2016 ◽  
Vol 6 (1) ◽  
Author(s):  
Guo-Ming Ho ◽  
Ci-Jhang Huang ◽  
Elise Yu-Tzu Li ◽  
Sheng-Kai Hsu ◽  
Ti Wu ◽  
...  
Keyword(s):  
Diels Alder ◽  
Normal Electron ◽  
Electron Demand

ChemInform Abstract: An Asymmetric Normal-Electron-Demand Aza-Diels-Alder Reaction via Trienamine Catalysis.

ChemInform ◽  
2014 ◽  
Vol 45 (17) ◽  
pp. no-no
Author(s):  
Jing-Xin Liu ◽  
Qing-Qing Zhou ◽  
Jin-Gen Deng ◽  
Ying-Chun Chen
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Normal Electron ◽  
Electron Demand

A Novel Application of the Diels—Alder Reaction: Nitronaphthalenes as Normal Electron Demand Dienophiles.

ChemInform ◽  
2007 ◽  
Vol 38 (32) ◽  
Author(s):  
Elisa Paredes ◽  
Romina Brasca ◽  
Maria Kneeteman ◽  
Pedro M. E. Mancini
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Normal Electron ◽  
Electron Demand

scholarly journals Antiaromaticity Gain Activates Tropone and Nonbenzenoid Aromatics as Normal-Electron-Demand Diels–Alder Dienes

2020 ◽  
Vol 22 (18) ◽  
pp. 7083-7087
Author(s):  
Lucas J. Karas ◽  
Adam T. Campbell ◽  
Igor V. Alabugin ◽  
Judy I. Wu
Keyword(s):  
Diels Alder ◽  
Normal Electron ◽  
Electron Demand

Normal electron demand Diels–Alder cycloaddition of indoles to 2,3-dimethyl-1,3-butadiene

Tetrahedron ◽  
2011 ◽  
Vol 67 (22) ◽  
pp. 3997-4001 ◽  
Author(s):  
M. Carmen de la Fuente ◽  
Domingo Domínguez
Keyword(s):  
Diels Alder ◽  
Normal Electron ◽  
Electron Demand

An asymmetric normal-electron-demand aza-Diels–Alder reaction via trienamine catalysis

2013 ◽  
Vol 11 (47) ◽  
pp. 8175 ◽  
Author(s):  
Jing-Xin Liu ◽  
Qing-Qing Zhou ◽  
Jin-Gen Deng ◽  
Ying-Chun Chen
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Normal Electron ◽  
Electron Demand

A novel application of the Diels–Alder reaction: nitronaphthalenes as normal electron demand dienophiles

Tetrahedron ◽  
2007 ◽  
Vol 63 (18) ◽  
pp. 3790-3799 ◽  
Author(s):  
Elisa Paredes ◽  
Romina Brasca ◽  
María Kneeteman ◽  
Pedro M.E. Mancini
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Normal Electron ◽  
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>

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