scholarly journals Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives

2014 ◽  
Vol 10 ◽  
pp. 929-935 ◽  
Author(s):  
Akshay Kumar ◽  
Swapandeep Singh Chimni
Keyword(s):  
Amino Acids ◽  
Sodium Borohydride ◽  
Michael Addition ◽  
High Yield ◽  
Michael Adduct ◽  
Michael Adducts ◽  
Primary Amino ◽  
The Michael Addition

Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version of the reaction by a domino Knoevenagel–Michael sequence. The Michael adduct 4a was transformed into spirooxindole 6 by a reduction with sodium borohydride in a highly enantioselective manner.

Novel ferrocene-based bifunctional amine–thioureas for asymmetric Michael addition of acetylacetone to nitroolefins

2015 ◽  
Vol 13 (17) ◽  
pp. 5054-5060 ◽  
Author(s):  
Xiaochen Ren ◽  
Chunyan He ◽  
Yingle Feng ◽  
Yonghai Chai ◽  
Wei Yao ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Efficient Method ◽  
Michael Addition ◽  
High Yield ◽  
Bifunctional Catalysts ◽  
Michael Adducts ◽  
Asymmetric Michael Addition ◽  
Multiple Hydrogen Bonding

An efficient method was developed to synthesize the ferrocene-based bifunctional amine–thioureas bearing multiple hydrogen-bonding donors. Asymmetric Michael addition of acetylacetone to nitroolefins catalyzed by these novel bifunctional catalysts affords the Michael adducts in high yield and moderate to excellent enantioselectivities.

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxy­benzophenone

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 607-616 ◽  
Author(s):  
Yuri Belokon ◽  
Zalina Gugkaeva ◽  
Vladimir Larionov ◽  
Margarita Moskalenko ◽  
Victor Khrustalev ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Bases ◽  
Methyl Acrylate ◽  
Michael Addition ◽  
Alkylation Reaction ◽  
Different Types ◽  
The Michael Addition

We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).

scholarly journals A Flavone Fluorescent Probe for Cysteine Detection

2019 ◽  
Vol 31 (12) ◽  
pp. 2909-2914
Author(s):  
Saleh N. Al-Busafi ◽  
Salma M. Al-Kindi ◽  
Fakhr Eldin O. Suliman ◽  
Aliya A. Al-Kalbani
Keyword(s):  
Amino Acids ◽  
Fluorescent Probe ◽  
1H Nmr ◽  
Michael Addition ◽  
Addition Reaction ◽  
Fluorescence Emission ◽  
Selective Detection ◽  
Michael Addition Reaction ◽  
Uv Visible ◽  
The Michael Addition

A new blue-emitting fluorescent probe 1 based on flavone structure was prepared for the selective detection of cysteine. The probe was prepared through three synthetic steps from commercially available starting materials. Selective detection of cysteine by probe 1 in the presence of other non-thiol amino acids was established by UV-visible and fluorescent experiments. A remarkable fluorescence emission was observed at 469 nm when cysteine was mixed with probe 1. The Michael addition reaction of cysteine to probe-1 was confirmed by 1H NMR technique.

scholarly journals Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones

2019 ◽  
Vol 15 ◽  
pp. 1289-1297 ◽  
Author(s):  
Alexander N Reznikov ◽  
Anastasiya E Sibiryakova ◽  
Marat R Baimuratov ◽  
Eugene V Golovin ◽  
Victor B Rybakov ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Bioactive Compounds ◽  
Michael Addition ◽  
Michael Reaction ◽  
High Yield ◽  
Michael Adducts ◽  
Significant Rate ◽  
Asymmetric Michael Addition ◽  
Stereogenic Centers ◽  
Asymmetric Michael Reaction

Functionally substituted sulfones with stereogenic centers are valuable reagents in organic synthesis and key motifs in some bioactive compounds. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. This reaction provides convenient access to non-racemic 4-nitro-2-sulfonylbutan-1-ones with two stereocenters with high yield and excellent enantioselectivity (up to 99%). It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but the Michael adducts may epimerize at the C-2 position at a significant rate. Conditions for the preparation of individual diastereomers were found.

ChemInform Abstract: On the Michael Addition of Water to α,β-Unsaturated Ketones Using Amino Acids.

ChemInform ◽  
2014 ◽  
Vol 45 (21) ◽  
pp. no-no
Author(s):  
Verena Resch ◽  
Christiane Seidler ◽  
Bi-Shuang Chen ◽  
Ian Degeling ◽  
Ulf Hanefeld
Keyword(s):  
Amino Acids ◽  
Michael Addition ◽  
Unsaturated Ketones ◽  
The Michael Addition

scholarly journals On the Michael Addition of Water to α,β-Unsaturated Ketones Using Amino Acids

2013 ◽  
Vol 2013 (34) ◽  
pp. 7697-7704 ◽  
Author(s):  
Verena Resch ◽  
Christiane Seidler ◽  
Bi-Shuang Chen ◽  
Ian Degeling ◽  
Ulf Hanefeld
Keyword(s):  
Amino Acids ◽  
Michael Addition ◽  
Unsaturated Ketones ◽  
The Michael Addition

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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