ChemInform Abstract: Enantioselective Allylic Amination of Morita-Baylis-Hillman Carbonates Catalyzed by Modified Cinchona Alkaloids.

ChemInform ◽  
2010 ◽  
Vol 41 (11) ◽  
pp. no-no
Author(s):  
Shan-Jun Zhang ◽  
Hai-Lei Cui ◽  
Kun Jiang ◽  
Rui Li ◽  
Zhen-Yu Ding ◽  
...  
Keyword(s):  
Cinchona Alkaloids ◽  
Allylic Amination

Enantioselective Allylic Amination of Morita-Baylis-Hillman Carbonates Catalysed by Modified Cinchona Alkaloids

2009 ◽  
Vol 2009 (33) ◽  
pp. 5804-5809 ◽  
Author(s):  
Shan-Jun Zhang ◽  
Hai-Lei Cui ◽  
Kun Jiang ◽  
Rui Li ◽  
Zhen-Yu Ding ◽  
...  
Keyword(s):  
Cinchona Alkaloids ◽  
Allylic Amination

scholarly journals New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

2019 ◽  
Vol 15 ◽  
pp. 830-839
Author(s):  
Iveta Chena Tichá ◽  
Simona Hybelbauerová ◽  
Jindřich Jindřich
Keyword(s):  
Click Reaction ◽  
Enantiomeric Excess ◽  
Cinchona Alkaloids ◽  
Cinchona Alkaloid ◽  
Cyclodextrin Derivatives ◽  
Allylic Amination ◽  
Asymmetric Syntheses ◽  
Wide Range ◽  
Enantioselective Reactions ◽  
Organocatalytic Reactions

The preparation of new organocatalysts for asymmetric syntheses has become a key stage of enantioselective catalysis. In particular, the development of new cyclodextrin (CD)-based organocatalysts allowed to perform enantioselective reactions in water and to recycle catalysts. However, only a limited number of organocatalytic moieties and functional groups have been attached to CD scaffolds so far. Cinchona alkaloids are commonly used to catalyze a wide range of enantioselective reactions. Thus, in this study, we report the preparation of new α- and β-CD derivatives monosubstituted with cinchona alkaloids (cinchonine, cinchonidine, quinine and quinidine) on the primary rim through a CuAAC click reaction. Subsequently, permethylated analogs of these cinchona alkaloid–CD derivatives also were synthesized and the catalytic activity of all derivatives was evaluated in several enantioselective reactions, specifically in the asymmetric allylic amination (AAA), which showed a promising enantiomeric excess of up to 75% ee. Furthermore, a new disubstituted α-CD catalyst was prepared as a pure AD regioisomer and also tested in the AAA. Our results indicate that (i) the cinchona alkaloid moiety can be successfully attached to CD scaffolds through a CuAAC reaction, (ii) the permethylated cinchona alkaloid–CD catalysts showed better results than the non-methylated CDs analogues in the AAA reaction, (iii) promising enantiomeric excesses are achieved, and (iv) the disubstituted CD derivatives performed similarly to monosubstituted CDs. Therefore, these new CD derivatives with cinchona alkaloids effectively catalyze asymmetric allylic aminations and have the potential to be successfully applied in other enantioselective reactions.

Allylic Amination via Acid Catalyzed Leaving Group Activation

2016 ◽  
Vol 3 (2) ◽  
pp. 145-159
Author(s):  
Marija Skvorcova ◽  
Aigars Jirgensons
Keyword(s):  
Allylic Amination ◽  
Leaving Group ◽  
Acid Catalyzed

ChemInform Abstract: Enantioselective Domino Heck-Allylic Amination Reactions.

ChemInform ◽  
2010 ◽  
Vol 30 (35) ◽  
pp. no-no
Author(s):  
Dietmar Flubacher ◽  
Guenter Helmchen
Keyword(s):  
Allylic Amination

Origin of Fast Catalysis in Allylic Amination Reactions Catalyzed by Pd–Ti Heterobimetallic Complexes

2015 ◽  
Vol 137 (23) ◽  
pp. 7371-7378 ◽  
Author(s):  
Whitney K. Walker ◽  
Benjamin M. Kay ◽  
Scott A. Michaelis ◽  
Diana L. Anderson ◽  
Stacey J. Smith ◽  
...  
Keyword(s):  
Allylic Amination ◽  
Heterobimetallic Complexes
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