scholarly journals Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones

2012 ◽  
Vol 8 ◽  
pp. 1279-1283 ◽  
Author(s):  
Chunhui Jiang ◽  
Fangrui Zhong ◽  
Yixin Lu
Keyword(s):  
Mannich Reaction ◽  
Keto Acids

The first decarboxylative Mannich reaction employing β-keto acids, catalyzed by cinchonine-derived bifunctional thiourea catalyst has been described. The desired β-amino ketones were obtained in excellent yields and with moderate to good enantioselectivities.

A Highly Diastereoselective Decarboxylative Mannich Reaction of β-Keto Acids with Optically Active N-Sulfinyl α-Imino Esters

2012 ◽  
Vol 14 (12) ◽  
pp. 3092-3095 ◽  
Author(s):  
Cui-Feng Yang ◽  
Chen Shen ◽  
Jian-Yong Wang ◽  
Shi-Kai Tian
Keyword(s):  
Mannich Reaction ◽  
Optically Active ◽  
Keto Acids ◽  
Imino Esters

Ni-catalyzed asymmetric decarboxylative Mannich reaction for the synthesis of β-trifluoromethyl-β-amino ketones

RSC Advances ◽  
2015 ◽  
Vol 5 (34) ◽  
pp. 26811-26814 ◽  
Author(s):  
Ping Qian ◽  
Yanling Dai ◽  
Haibo Mei ◽  
Vadim A. Soloshonok ◽  
Jianlin Han ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Keto Acids

A Ni-catalyzed asymmetric decarboxylative Mannich reaction between (Ss)-N-t-butylsulfinyl-3,3,3-trifluoro-acetaldimine and β-keto-acids was reported, affording β-trifluoromethyl-β-amino ketones with excellent yields and diastereoselectivities.

Enantioselective Decarboxylative Mannich Reaction of β-Keto acids with C-Alkynyl N-Boc N,O-Acetals: Access to Chiral β-Keto Propargylamines

2021 ◽  
Author(s):  
Congcong Zhang ◽  
Lijun Chen ◽  
baochun shen ◽  
Huiding Xie ◽  
Wei Li ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Multifunctional Compounds ◽  
Keto Acids ◽  
Synthetic Approaches

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain...

Withdrawal Notice: Organocatalyzed Asymmetric Mannich Reaction: An Update

2020 ◽  
Vol 24 ◽  
Author(s):  
Ilnaz Baagheri ◽  
Leila Mohammadi ◽  
Vahideh Zadsirjan ◽  
Majid M. Heravi
Keyword(s):  
Organic Chemistry ◽  
Mannich Reaction ◽  
Editorial Policy ◽  
Editorial Policies ◽  
Copyright Permission ◽  
Legal Right

The article has been withdrawn at the request of editor of the journal Current Organic Chemistry: Bentham Science apologizes to the readers of the journal for any inconvenience this may have caused. The Bentham Editorial Policy on Article The Bentham Editorial Policy on Article Withdrawal can be found at https://benthamscience.com/editorial-policies-main.php BENTHAM SCIENCE DISCLAIMER: It is a condition of publication that manuscripts submitted to this journal have not been published and will not be simultaneously submitted or published elsewhere. Furthermore, any data, illustration, structure or table that has been published elsewhere must be reported, and copyright permission for reproduction must be obtained. Plagiarism is strictly forbidden, and by submitting the article for publication the authors agree that the publishers have the legal right to take appropriate action against the authors, if plagiarism or fabricated information is discovered. By submitting a manuscript, the authors agree that the copyright of their article is transferred to the publishers if and when the article is accepted for publication.

Construction the A-B bicyclic ring structure of Stemocurtisisne

2020 ◽  
Vol 17 ◽  
Author(s):  
Duc Dau Xuan
Keyword(s):  
Glutamic Acid ◽  
Natural Product ◽  
Mannich Reaction ◽  
Boronic Acid ◽  
Ring Opening ◽  
Ring Structure ◽  
Starting Material ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

: The synthesis of the A-B bicyclic ring structure 3 of the natural product Stemocurtisine is described. The synthesis was accomplished in seven synthetic steps from commercially available L-glutamic acid. The key step involved a borono-Mannich reaction between the hemiaminal 6 and trans-β-styryl boronic acid and trans-β-styrylpotassiumtrifluoroborate to prepare the cis diene 4. Attempts to prepare the A-B-C ring compound 2 via intramolecular epoxide ring opening followed by rearangement under different basic conditions were unsuccessful. Only unreactive starting material was recovered.

Synthesis of Novel 8-Hydroxyquinoline Derivatives through Mannich Reaction and their Biological Evaluation as Potential Immunomodulatory Agents

2020 ◽  
Vol 16 (4) ◽  
pp. 531-543
Author(s):  
Shaheen Faizi ◽  
Tahira Sarfaraz ◽  
Saima Sumbul ◽  
Almas Jabeen ◽  
Sobia A. Halim ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Aromatic Aldehydes ◽  
Mannich Bases ◽  
Biological Evaluation ◽  
Mechanism Of Inhibition ◽  
Potent Inhibition ◽  
Tnf Α ◽  
Elisa Technique ◽  
Factor Α ◽  
New Compounds

Background: In continuation of our work on Mannich reaction on 8-hydroxyquinoline, fifteen different combinations of aromatic aldehydes and aniline were subjected to Mannich reaction from which twelve products (eight Mannich bases, two imines and two intramolecularly cyclized products with benzofuranone skeleton) were obtained. Among them six compounds (1, 2, 6, 8, 9 and 12) are the new compounds. The structures of the compounds were characterized by UV, IR, MS and 1H NMR. Method: The compounds were tested for the inhibition of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and Interleukin-1β (IL-1β) at a concentration of 25 µg/mL. The cytokines were produced by THP-1 cells differentiated with PMA for 24hrs and stimulated with LPS for 4 hrs and supernatant were analyzed through ELISA technique. Results and Discussion: Compounds 1-5, 8 and 9 inhibited the production of TNF-α and IL-1β. Compounds 1, 3, and 8 exerted potent inhibitions of TNF-α with 71%, 71%, and 83% inhibition, respectively. Compounds 1 and 8 significantly inhibited the production of IL-1β with 64% and 78% inhibition, respectively. Conclusion: Compounds 1 and 8 significantly inhibited the production of IL-1β with 64% and 78% inhibition, respectively. Notably compound 8 showed the most potent inhibition of these cytokines. Additionally, the effect of compounds on viability of THP-1 cells was also evaluated. Moreover, molecular docking was carried out to study the mechanism of inhibition of TNF-α production.

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