scholarly journals Asymmetric 1,4-Michael Addition Reaction of Azadienes with α-Thiocyanoindanones Catalyzed by Bifunctional Chiral Squaramide

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5146
Author(s):  
Xiao-Yan Dong ◽  
Da-Ming Du
Keyword(s):  
Reaction Mechanism ◽  
Michael Addition ◽  
Addition Reaction ◽  
Quaternary Carbon ◽  
Michael Addition Reaction ◽  
First Case ◽  
Scope Of Application

In this paper, the organocatalytic asymmetric 1,4-Michael addition reaction of azadienes and α-thiocyanoindanones was investigated. A series of chiral benzofuran compounds containing thiocyano group and quaternary carbon center were synthesized in moderate yields with good enantioselectivities (up to 90:10 er) and high diastereoselectivities (up to >95:5 dr). This is the first case of 1,4-Michael addition reaction using α-thiocyanoindanones to obtain a series of chiral thiocyano compounds and further broaden the scope of application of azadiene substrates. In addition, a possible reaction mechanism is also described in the article.

scholarly journals Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity

2012 ◽  
Vol 8 ◽  
pp. 1485-1498 ◽  
Author(s):  
Tatyana E Shubina ◽  
Matthias Freund ◽  
Sebastian Schenker ◽  
Timothy Clark ◽  
Svetlana B Tsogoeva
Keyword(s):  
Reaction Mechanism ◽  
Dft Calculations ◽  
Solvent Effects ◽  
Michael Addition ◽  
Michael Reaction ◽  
Addition Reaction ◽  
Diethyl Malonate ◽  
Theoretical Studies ◽  
Michael Addition Reaction ◽  
The Michael Addition

A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-β-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations provide a plausible description of the reaction mechanism.

scholarly journals NMR spectroscopy study on N,N′-bismaleimide-4,4′-diphenylmethane and barbituric acid synthesis reaction mechanism in N,N′-dimethylformamide solvent

RSC Advances ◽  
2017 ◽  
Vol 7 (2) ◽  
pp. 651-661
Author(s):  
Yuan-Chun Wen ◽  
Yuan-Chun Sue ◽  
Shan-Yuan Yang ◽  
Jing-Pin Pan ◽  
Tsung-Hsiung Wang ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Nmr Spectroscopy ◽  
Michael Addition ◽  
Barbituric Acid ◽  
Addition Reaction ◽  
Acid Synthesis ◽  
Synthesis Reaction ◽  
Spectroscopy Study ◽  
Michael Addition Reaction

1H signal assignments of C1N0E, C1N0K, C2N0A, C2N0S model products of Michael addition reaction in STOBA-like 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.

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones via dual α′,α′-C(sp3)–H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones

2018 ◽  
Vol 16 (48) ◽  
pp. 9461-9471 ◽  
Author(s):  
Jiayong Zhang ◽  
Zhiwei Miao
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction

A sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones afforded cyclopentanone-fused spiro-pyrazolones catalyzed by DPPB via dual α′,α′-C(sp3)–H bifunctionalization.

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