Chiral auxiliary-mediated asymmetric induction in a thermal inverse electron demand hetero-Diels-Alder reaction. Enantioselective synthesis of the taxol A-ring side chain

1993 ◽  
Vol 58 (22) ◽  
pp. 5889-5891 ◽  
Author(s):  
Charles S. Swindell ◽  
Ming Tao
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Chiral Auxiliary ◽  
Asymmetric Induction ◽  
Side Chain ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

scholarly journals Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions

2014 ◽  
Vol 10 ◽  
pp. 282-286 ◽  
Author(s):  
Salah Fadel ◽  
Youssef Hajbi ◽  
Mostafa Khouili ◽  
Said Lazar ◽  
Franck Suzenet ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Aryl Halides ◽  
Side Chain ◽  
Terminal Alkyne ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Cross Coupling Reaction ◽  
Electron Demand

Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels–Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route.

Enantioselective Synthesis of cis ‐Decalin Derivatives by the Inverse‐Electron‐Demand Diels–Alder Reaction of 2‐Pyrones

2020 ◽  
Vol 132 (42) ◽  
pp. 18570-18575
Author(s):  
Xu‐Ge Si ◽  
Zhi‐Mao Zhang ◽  
Cheng‐Gong Zheng ◽  
Zhan‐Ting Li ◽  
Quan Cai
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(iii)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction

2015 ◽  
Vol 51 (18) ◽  
pp. 3835-3837 ◽  
Author(s):  
Haipeng Hu ◽  
Yangbin Liu ◽  
Jing Guo ◽  
Lili Lin ◽  
Yali Xu ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Quinone Methides ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

An asymmetric inverse-electron-demand hetero-Diels–Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N′-dioxide–Sc(iii) complex as the catalyst.

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