Highly enantioselective Michael addition reactions of 2-substituted benzofuran-3(2H)-ones to nitroolefins

2015 ◽  
Vol 13 (39) ◽  
pp. 9943-9947 ◽  
Author(s):  
Zhi-Pei Zhang ◽  
Nan Dong ◽  
Xin Li ◽  
Jin-Pei Cheng
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Addition Reactions ◽  
Michael Addition Reaction

A highly enantioselective Michael addition reaction of 2-substituted benzofuran-3(2H)-ones to nitroolefins was promoted by a bifunctional squaramide catalyst.

Synthesis of functionalized isoxazole–oxindole hybrids via on water, catalyst free vinylogous Henry and 1,6-Michael addition reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (100) ◽  
pp. 81768-81773 ◽  
Author(s):  
Sakkani Nagaraju ◽  
Neeli Satyanarayana ◽  
Banoth Paplal ◽  
Anuji K. Vasu ◽  
Sriram Kanvah ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Addition Reactions ◽  
Michael Addition Reaction ◽  
Henry Reaction ◽  
Catalyst Free

Various isoxazole–oxindole hybrids were synthesized via vinylogous Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin under catalyst free conditions in water. The products obtained were functionalized using 1,6-Michael addition reaction.

Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones

2017 ◽  
Vol 15 (29) ◽  
pp. 6089-6092 ◽  
Author(s):  
Feng Yin ◽  
Ainash Garifullina ◽  
Fujie Tanaka
Keyword(s):  
Carboxylic Acid ◽  
Michael Addition ◽  
Addition Reaction ◽  
Reaction System ◽  
Addition Reactions ◽  
Michael Addition Reaction ◽  
Asymmetric Michael Addition

An enantioselective Michael addition reaction system was developed. Using the reaction system, 5-methylpyrrolidine-3-carboxylic acid was synthesized in two steps.

Preparation of a chiral Pt12 tetrahedral cage and its use in catalytic Michael addition reaction

2018 ◽  
Vol 54 (38) ◽  
pp. 4814-4817 ◽  
Author(s):  
Imtiyaz Ahmad Bhat ◽  
Anthonisamy Devaraj ◽  
Prodip Howlader ◽  
Ki-Whan Chi ◽  
Partha Sarathi Mukherjee
Keyword(s):  
Michael Addition ◽  
Self Assembly ◽  
Addition Reaction ◽  
Addition Reactions ◽  
Stoichiometric Ratio ◽  
Michael Addition Reaction ◽  
Methanol Mixture ◽  
Hexadentate Ligand ◽  
The Michael Addition

A chiral M12L4 molecular tetrahedron (T) was synthesized by self-assembly of chiral cis-[(1S,2S)-dch]Pt(NO3)2 (M) with a hexadentate ligand (L) in 3 : 1 stoichiometric ratio. The cage T was found to catalyze the Michael addition reactions of series of nitrostyrene derivatives with indole in (9 : 1) water–methanol mixture.

Theoretical free energy profile and benchmarking of functionals for amino-thiourea organocatalyzed nitro-Michael addition reaction

2020 ◽  
Vol 22 (20) ◽  
pp. 11529-11536 ◽  
Author(s):  
Josefredo R. Pliego
Keyword(s):  
Free Energy ◽  
Michael Addition ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Catalytic Process ◽  
Addition Reactions ◽  
Energy Profile ◽  
Michael Addition Reaction ◽  
Free Energy Profile

Amino-thiourea organocatalysis is an important catalytic process for enantioselective conjugate addition reactions.

Zinc complexes supported by pyridine-N-oxide ligands: synthesis, structures and catalytic Michael addition reactions

2020 ◽  
Vol 49 (35) ◽  
pp. 12365-12371
Author(s):  
Xiu-Fang Mo ◽  
Chang-Feng Xiong ◽  
Ze-Wen Chen ◽  
Chao Liu ◽  
Piao He ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Michael Addition ◽  
Addition Reaction ◽  
Zinc Complexes ◽  
Addition Reactions ◽  
Michael Addition Reaction ◽  
Highly Efficient

Zinc complexes supported by pyridine-N-oxide ligands show highly efficient catalysis for Michael addition reaction. The NMR and MS experiments analysis displays intermediate [Zn(SR)2(HSR)4] has real catalytic activity for the addition reactions.

scholarly journals Asymmetric Michael addition reactions of pyrrolones with chalcones catalyzed by vicinal primary-diamine salts

RSC Advances ◽  
2017 ◽  
Vol 7 (39) ◽  
pp. 24547-24550 ◽  
Author(s):  
Xiaolei Du ◽  
Dawei Yin ◽  
Zemei Ge ◽  
Xin Wang ◽  
Runtao Li
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Addition Reactions ◽  
Michael Addition Reaction ◽  
Asymmetric Michael Addition

The asymmetric Michael addition reaction of pyrrolones with chalcones catalyzed by vicinal primary-diamine salts has been developed in good yields and high enantioselectivities.

Sulfonic acid-functionalized magnetic nanoparticles as a recyclable and eco-friendly catalyst for atom economical Michael addition reactions and bis indolyl methane synthesis

RSC Advances ◽  
2015 ◽  
Vol 5 (4) ◽  
pp. 3023-3030 ◽  
Author(s):  
Hajar Mahmoudi ◽  
Abbas Ali Jafari ◽  
Soroosh Saeedi ◽  
Habib Firouzabadi
Keyword(s):  
Magnetic Nanoparticles ◽  
Michael Addition ◽  
Sulfonic Acid ◽  
Addition Reaction ◽  
Addition Reactions ◽  
Michael Addition Reaction ◽  
Functionalized Magnetic Nanoparticles

Sulfonic acid-functionalized magnetic nanoparticles as a recyclable and eco-friendly catalyst for atom economical Michael addition reaction and bis indolyl methane synthesis.

Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

2019 ◽  
Author(s):  
Nobutaka Fujieda ◽  
Miho Yuasa ◽  
Yosuke Nishikawa ◽  
Genji Kurisu ◽  
Shinobu Itoh ◽  
...  
Keyword(s):  
Michael Addition ◽  
In Silico ◽  
Addition Reaction ◽  
Single Point ◽  
Point Mutations ◽  
Unsaturated Ketone ◽  
Michael Addition Reaction ◽  
Beta Barrel ◽  
Cupin Superfamily ◽  
Single Point Mutations

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

scholarly journals Recoverable Phospha-Michael Additions Catalyzed by a 4-N,N-Dimethylaminopyridinium Saccharinate Salt or a Fluorous Long-Chained Pyridine: Two Types of Reusable Base Catalysts

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1159
Author(s):  
Eskedar Tessema ◽  
Vijayanath Elakkat ◽  
Chiao-Fan Chiu ◽  
Jing-Hung Zheng ◽  
Ka Long Chan ◽  
...  
Keyword(s):  
Michael Addition ◽  
Polar Solvent ◽  
Addition Reaction ◽  
High Yield ◽  
Addition Reactions ◽  
Polar Solvents ◽  
Unsaturated Bond ◽  
Base Catalysts ◽  
Michael Additions

Phospha-Michael addition, which is the addition reaction of a phosphorus-based nucleophile to an acceptor-substituted unsaturated bond, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds, since many different electrophiles and P nucleophiles can be combined with each other. This offers the possibility to access many diversely functionalized products. In this work, two kinds of basic pyridine-based organo-catalysts were used to efficiently catalyze phospha-Michael addition reactions, the 4-N,N-dimethylaminopyridinium saccharinate (DMAP·Hsac) salt and a fluorous long-chained pyridine (4-Rf-CH2OCH2-py, where Rf = C11F23). These catalysts have been synthesized and characterized by Lu’s group. The phospha-Michael addition of diisopropyl, dimethyl or triethyl phosphites to α, β-unsaturated malonates in the presence of those catalysts showed very good reactivity with high yield at 80–100 °C in 1–4.5 h with high catalytic recovery and reusability. With regard to significant catalytic recovery, sometimes more than eight cycles were observed for DMAP·Hsac adduct by using non-polar solvents (e.g., ether) to precipitate out the catalyst. In the case of the fluorous long-chained pyridine, the thermomorphic method was used to efficiently recover the catalyst for eight cycles in all the reactions. Thus, the easy separation of the catalysts from the products revealed the outstanding efficacy of our systems. To our knowledge, these are good examples of the application of recoverable organo-catalysts to the DMAP·Hsac adduct by using non-polar solvent and a fluorous long-chained pyridine under the thermomorphic mode in phospha-Michael addition reactions.

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