scholarly journals Hierarchically assembled helicates as reaction platform – From stoichiometric Diels-Alder reactions to enamine catalysis

2020 ◽  
Author(s):  
David Van Craen ◽  
Jenny Begall ◽  
Johannes Grosskurth ◽  
Leonard Himmel ◽  
Oliver Linnenberg ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Michael Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Ligands ◽  
Chiral Induction ◽  
Diels Alder Reaction ◽  
Enamine Catalysis ◽  
Stoichiometric Reaction

The stereoselectivity of a Diels-Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands is investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile are carefully varied. Based on the results of the stoichiometric reaction a secondary amine catalyzed nitro-Michael reaction is performed as well which affords reasonable diastereoselectivities.

scholarly journals Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis

2020 ◽  
Vol 16 ◽  
pp. 2338-2345
Author(s):  
David Van Craen ◽  
Jenny Begall ◽  
Johannes Großkurth ◽  
Leonard Himmel ◽  
Oliver Linnenberg ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Michael Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Ligands ◽  
Chiral Induction ◽  
Diels Alder Reaction ◽  
Enamine Catalysis ◽  
Stoichiometric Reaction

The stereoselectivity of a Diels–Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands was investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile were carefully varied. Based on the results of the stoichiometric reaction, a secondary amine-catalyzed nitro-Michael reaction is performed as well which afforded reasonable diastereoselectivities.

Direct access to pyrimidines through organocatalytic inverse-electron-demand Diels–Alder reaction of ketones with 1,3,5-triazine

RSC Advances ◽  
2015 ◽  
Vol 5 (94) ◽  
pp. 76759-76763 ◽  
Author(s):  
Gongming Yang ◽  
Qianfa Jia ◽  
Lei Chen ◽  
Zhiyun Du ◽  
Jian Wang
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Direct Access ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Enamine Catalysis ◽  
Electron Demand

An organocatalytic inverse-electron-demand Diels–Alder reaction of ketones with 1,3,5-triazine through enamine catalysis has been developed.

Sign in / Sign up

Export Citation Format

Share Document