scholarly journals First Zinc Bromide Promoted Annulative Domino Reactions between Enamines and Cyclic Morita–Baylis–Hillman Alcohols: Synthesis of N,O-Ketals

Synlett ◽  
2020 ◽  
Vol 31 (13) ◽  
pp. 1282-1286
Author(s):  
Farhat Rezgui ◽  
Ghalia Bouhalleb ◽  
Ahmed Meddeb ◽  
Noura Fakhar Bourguiba ◽  
Julien Legros ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Conjugate Addition ◽  
Domino Reaction ◽  
Domino Reactions ◽  
Zinc Bromide ◽  
Iminium Ion

A new efficient ZnBr2-mediated annulative domino reaction between enamines and cyclic Morita–Baylis–Hillman (MBH) alcohols is disclosed. The process involves a tandem sequence (intermolecular conjugate addition of enamines to MBH alcohols and intramolecular nucleophilic addition of the hydroxyl moiety to the transiently generated iminium ion), affording the corresponding N,O-ketals diastereoselectively in good yields.

scholarly journals Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingguang Li ◽  
Meng Duan ◽  
Peiyuan Yu ◽  
K. N. Houk ◽  
Jianwei Sun
Keyword(s):  
Hydrogen Bonding ◽  
Phosphoric Acid ◽  
Nucleophilic Addition ◽  
Acid Catalysis ◽  
Conjugate Addition ◽  
Mild Conditions ◽  
Rapid Construction ◽  
Chiral Phosphoric Acid ◽  
Cyclic Molecules ◽  
Selectivity Control

AbstractCatalytic asymmetric dearomatization (CADA) is a powerful tool for the rapid construction of diverse chiral cyclic molecules from cheap and easily available arenes. This work reports an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition. By suitable stabilization of the thiophenyl carbocation with an indole motif in the form of indole imine methide, excellent remote chemo-, regio-, and stereocontrol in the nucleophilic addition can be achieved with chiral phosphoric acid catalysis under mild conditions. This protocol can be successfully extended to the asymmetric dearomatization of other heteroarenes including selenophenes and furans. Control experiments and DFT calculations demonstrate a possible pathway in which hydrogen bonding plays an important role in selectivity control.

Are fermentation products promising feedstock for high-density bio-fuel? domino reactions for upgrading aqueous acetone–butanol–ethanol mixtures

2020 ◽  
Vol 22 (18) ◽  
pp. 6137-6147
Author(s):  
Yahui Gong ◽  
Pingzhou Wang ◽  
Cai Wu ◽  
Jie Wang ◽  
Chun Shen
Keyword(s):  
Aqueous Acetone ◽  
High Density ◽  
Domino Reaction ◽  
Domino Reactions ◽  
Fermentation Products ◽  
Acetone Butanol Ethanol

Upgrading aqueous acetone–butanol–ethanol mixtures to high-density bio-fuels is realized via the three-step domino reaction in a green way.

Rhodium(III)-Catalyzed C-H Alkylation/Nucleophilic Addition Domino Reaction

2018 ◽  
Vol 2019 (4) ◽  
pp. 660-664 ◽  
Author(s):  
Mengyao Tang ◽  
Yunpeng Li ◽  
Shengnan Han ◽  
Lei Liu ◽  
Lutz Ackermann ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Domino Reaction

Asymmetric Thio-Michael/Nucleophilic Addition Domino Reaction with ChiralN-Sulfinimines

2007 ◽  
Vol 72 (9) ◽  
pp. 3569-3572 ◽  
Author(s):  
Akio Kamimura ◽  
Hidenori Okawa ◽  
Yuki Morisaki ◽  
Shingo Ishikawa ◽  
Hidemitsu Uno
Keyword(s):  
Nucleophilic Addition ◽  
Domino Reaction

Gold-catalyzed domino reactions of alkynol and p-quinone methides: divergent synthesis of fused- and spiro-ketals

2020 ◽  
Vol 7 (6) ◽  
pp. 856-861 ◽  
Author(s):  
Wenxiu Mao ◽  
Shiquan Lin ◽  
Liang Zhang ◽  
Haifeng Lu ◽  
Jiong Jia ◽  
...  
Keyword(s):  
Domino Reaction ◽  
Domino Reactions ◽  
Quinone Methides

A gold-catalyzed domino reaction of alkynyl alcohols and p-quinone methides to obtain divergent fused- and spiro-ketals has been developed.

Domino Reactions of Chromones with Heterocyclic Enamines

Synlett ◽  
2021 ◽  
Author(s):  
Peter Langer
Keyword(s):  
Carbon Atom ◽  
Carbonyl Group ◽  
Functional Groups ◽  
Conjugate Addition ◽  
Heterocyclic Ring ◽  
Ring Cleavage ◽  
Domino Reactions ◽  
Chromone Derivatives ◽  
Convenient Synthesis ◽  
Heterocyclic Enamines

AbstractDomino reactions of heterocyclic enamines with chromone derivatives provides a convenient synthesis of a great variety of annulated heterocyclic ring systems. The course of the reaction depends on the type of substituent located at position 3 of the chromone. Reactions of 3-unsubstituted chromones, 3-nitrochromones, and 3-halochromones proceed by conjugate addition of the carbon atom of the enamine to carbon C-2 of the chromone, ring cleavage, and recyclization via the chromone carbonyl group. In the case of 3-formylchromes, 3-dichloroacetylchromone, 3-perfluoroalkanoylthiochromones, 3-(2-fluorobenzoyl)chromones, and 3-methoxalylchromones the final cyclization proceeds via the carbonyl group located outside the chromone moiety. The functional groups located at the carbonyl group at position 3 of the chromone allow for further synthetic transformations including additional ring closures.Contents1 Introduction2 3-Unsubstituted Chromones3 3-Nitrochromones4 3-Formylchromes5 3-Dichloroacetylchromone6 3-Perfluoroalkanoylthiochromones7 3-Methoxalylchromones8 3-(2-Fluorobenzoyl)chromones9 3-Halochromones10 Chromone-3-carboxylic Acids11 Conclusions

Domino Reactions of 1-Aroyl-3,4-dihydroisoquinolines with α,β-Unsaturated Aldehydes

Synthesis ◽  
2017 ◽  
Vol 49 (23) ◽  
pp. 5251-5257 ◽  
Author(s):  
Maria Matveeva ◽  
Tatiana Borisova ◽  
Alexander Titov ◽  
Lada Anikina ◽  
Svetlana Dyachenko ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Domino Reaction ◽  
Domino Reactions ◽  
Efficient Synthesis ◽  
Unsaturated Aldehydes

An efficient synthesis of pyrrolo[2,1-a]isoquinolines by a domino reaction from a variety of 3,4-dihydropyrrolo[2,1-a]isoquinolines and α,β-unsaturated aldehydes in the absence of catalyst in good yields under microwave irradiation, is reported.

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