Diastereoselectivity in a cyclic secondary amine catalyzed asymmetric Mannich reaction: a model rationalization from DFT studies

2018 ◽  
Vol 5 (14) ◽  
pp. 2148-2157 ◽  
Author(s):  
Siwei Shu ◽  
Zhao Liu ◽  
Yukui Li ◽  
Zhuofeng Ke ◽  
Yan Liu
Keyword(s):  
Secondary Amine ◽  
Mannich Reaction ◽  
Dft Studies ◽  
Detailed Structure ◽  
Mannich Reactions

DFT studies revealed the detailed structure stereoselectivity relationship for cyclic secondary amine catalyzed asymmetric Mannich reactions.

scholarly journals Recent advances and prospects in the Zn-catalysed Mannich reaction

RSC Advances ◽  
2021 ◽  
Vol 11 (16) ◽  
pp. 9098-9111
Author(s):  
Salahudeen Shamna ◽  
C. M. A. Afsina ◽  
Rose Mary Philip ◽  
Gopinathan Anilkumar
Keyword(s):  
Carbonyl Compound ◽  
Secondary Amine ◽  
Mannich Reaction ◽  
Mannich Base ◽  
Mannich Reactions ◽  
Recent Advances ◽  
Primary Secondary Amine

Amino alkylation of an acidic α-proton of a carbonyl by formaldehyde and a primary/secondary amine or ammonia, affording a β-amino-carbonyl compound also known as a Mannich base is a valuable reaction. We focus on recent advances in Zn catalysed Mannich reactions.

Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines

2019 ◽  
Vol 17 (30) ◽  
pp. 7182-7191 ◽  
Author(s):  
Qing-Da Zhang ◽  
Bo-Liang Zhao ◽  
Bing-Yu Li ◽  
Da-Ming Du
Keyword(s):  
Mannich Reaction ◽  
Mannich Reactions ◽  
Quaternary Stereocenters

Squaramide-catalyzed asymmetric Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines afforded fluorinated amino-pyrazolone-oxindoles with two quaternary stereocenters in good to excellent yields with excellent stereoselectivities.

Polyelectrolyte Brønsted acid catalyzed three-component Mannich reactions accelerated by emulsion

RSC Advances ◽  
2016 ◽  
Vol 6 (45) ◽  
pp. 39343-39347 ◽  
Author(s):  
Xi Chen ◽  
Huaming Sun ◽  
Yanlong Luo ◽  
Yajun Jian ◽  
Ya Wu ◽  
...  
Keyword(s):  
Polyacrylic Acid ◽  
Mannich Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Mannich Reactions ◽  
Brönsted Acid ◽  
Acid Catalyzed

An effective polyelectrolyte Brønsted acid (polyacrylic acid) catalyzed three-component Mannich reaction accelerated by emulsion has been developed.

A versatile access to vicinal diamine motifs by highly anti-selective asymmetric vinylogous Mannich reactions: an efficient total synthesis of (+)-absouline

2016 ◽  
Vol 3 (6) ◽  
pp. 683-692 ◽  
Author(s):  
Jian-Liang Ye ◽  
Hang Chen ◽  
Yu-Feng Zhang ◽  
Pei-Qiang Huang
Keyword(s):  
Total Synthesis ◽  
Mannich Reaction ◽  
Efficient Synthesis ◽  
Mannich Reactions

An anti-stereoselective vinylogous Mannich reaction between 2-TBSO-pyrrole and N-tert-butanesulfinyl imines and its application to the efficient synthesis of (+)-absouline were reported.

A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis

2015 ◽  
Vol 51 (71) ◽  
pp. 13694-13697 ◽  
Author(s):  
Francesco Berti ◽  
Federico Malossi ◽  
Fabio Marchetti ◽  
Mauro Pineschi
Keyword(s):  
Secondary Amine ◽  
Mannich Reaction ◽  
Enantioselective Synthesis ◽  
Bronsted Acids ◽  
Acyliminium Ions ◽  
Synergistic Catalysis

A novel enantioselective synthesis of carbamoyl isoquinoline and tetrahydropyridine derivatives is accomplished using matched combinations of Lewis or Brønsted acids and secondary amine organocatalysts.

Diaryliodonium salts as efficient Lewis acid catalysts for direct three component Mannich reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (32) ◽  
pp. 25485-25488 ◽  
Author(s):  
Yanxia Zhang ◽  
Jianwei Han ◽  
Zhen-Jiang Liu
Keyword(s):  
Lewis Acid ◽  
Mannich Reaction ◽  
Solvent Free ◽  
Acid Catalysts ◽  
Lewis Acid Catalysts ◽  
Mannich Reactions ◽  
Highly Active ◽  
Diaryliodonium Salts ◽  
Solvent Free Conditions

Diaryliodonium(iii) salts, as highly active and versatile Lewis acid catalysts for the direct three component Mannich reaction under solvent free conditions, have been investigated.

Catalyst-free Synthesis of Aminomethylphenol Derivatives in Cyclopentyl Methyl Ether via Petasis Borono-Mannich Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Jia-Qi Di ◽  
Hao-Jie Wang ◽  
Zhen-Shui Cui ◽  
Jin-Yong Hu ◽  
Zhan-Hui Zhang
Keyword(s):  
Secondary Amine ◽  
Methyl Ether ◽  
Mannich Reaction ◽  
Phenylboronic Acid ◽  
Functional Materials ◽  
Practical Method ◽  
Model Reaction ◽  
Arylboronic Acid ◽  
Reaction Conditions ◽  
Catalyst Free

Objective: Aminomethylphenol molecules have wider applications in pharmaceuticals, agrochemicals, plant protection and promising functional materials. The development of an efficient and practical method to prepare this class of compound is highly desirable from both environmental and economical points of views. Materials and Methods: In order to establish an effective synthetic method for preparing aminomethylphenol derivatives, the Petasis borono-Mannich reaction of salicylaldehyde, phenylboronic acid and 1,2,3,4-tetrahydroisoquinoline was selected as a model reaction. A variety of reaction conditions are investigated including solvent and temperature. The generality and limitation of the established method were also evaluated. Results and Discussion: It was found that model reaction can be carried out in cyclopentyl methyl ether at 80 oC under catalyst-free condition. This protocol with a broad substrate applicability, the reaction of various arylboronic acid, secondary amine and salicylaldehyde proceeded smoothly under optimal reaction conditions to afforded various aminomethylphenol derivatives in high yields. A practical, scalable, and high-yielding synthesis of aminomethylphenol derivatives was successfully accomplished. Conclusion: A catalyst-free practical method for the synthesis of minomethylphenol derivatives based on Petasis borono– Mannich (PBM) reaction of various arylboronic acid, secondary amine and salicylaldehyde in cyclopentyl methyl ether has been developed. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use cyclopentyl methyl ether as the reaction medium, clean reaction profiles, easy operation, and high to excellent yield.

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