Double Asymmetric Intramolecular aza-Michael Reaction: a Convenient Strategy for the Synthesis of Quinolizidine Alkaloids

2021 ◽  
Author(s):  
Javier Torres Fernández ◽  
Marcos Escolano ◽  
Gloria Alzuet ◽  
Maria Sanchez-Rosello ◽  
Carlos del Pozo Losada
Keyword(s):  
Michael Reaction ◽  
Quinolizidine Alkaloids ◽  
Michael Reactions

A new methodology to access the quinolizidine skeleton in an asymmetric fashion was devised. It involves two consecutive intramolecular aza-Michael reactions of sulfinyl amines bearing a bis-enone moiety, in turn...

scholarly journals Beneficial Contribution of Biosourced Ionic Liquids and Microwaves in the Michael Reaction

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 814
Author(s):  
Katia Bacha ◽  
Kawther Aguibi ◽  
Jean-Pierre Mbakidi ◽  
Sandrine Bouquillon
Keyword(s):  
Ionic Liquids ◽  
Reaction Time ◽  
Michael Reaction ◽  
Chiral Ionic Liquids ◽  
Michael Reactions ◽  
Basic Catalysts ◽  
The Michael Reaction

We developed a synthesis of chiral ionic liquids from proline and one of its derivatives. Nine chiral ionic liquids were synthesized with yields from 78% to 95%. These synthesized ionic liquids played two roles in Michael reactions, as solvents, and as basic catalysts, where the ionic phase could also be reused at least five times without loss of activity. The yields up to 99% were improved by increasing the amount of dimethylmalonate from 1.2 equivalents to 3 or 4 equivalents. Furthermore, the reaction time could be reduced from 24 h to 45 min through microwaves activation.

scholarly journals Recent Advance of Domino Michael Reaction in Natural Product Synthesis

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110498
Author(s):  
Hisahiro Hagiwara
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Michael Reaction ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Michael Reactions ◽  
Recent Advances ◽  
Key Steps ◽  
Related Compounds

Recent advances in the total syntheses of cyclic natural products and related compounds from 2005 to 2021, which employ domino Michael reactions as key steps, have been reviewed, focusing mainly on the domino Michael reactions catalyzed by organocatalysts.

scholarly journals Photochemically Activated Thiol-Michael Reactions via a Photolatent N-Heterocyclic Carbene

2019 ◽  
Author(s):  
Abraham Chemtob ◽  
Bao Tram Vu Ngoc ◽  
Julien Pinaud ◽  
Patrick Lacroix-Desmazes ◽  
Valérie Héroguez
Keyword(s):  
Michael Reaction ◽  
High Sensitivity ◽  
Heterocyclic Carbenes ◽  
Addition Reactions ◽  
H Nmr ◽  
Michael Reactions ◽  
Two Component ◽  
Step Growth ◽  
Step Growth Polymerization ◽  
Spectroscopy Optical

<p>While N-heterocyclic carbenes (NHCs) have proven highly effective in various polymerization reactions, the drawback is their high sensitivity towards air and water, which necessitates handling under rigorously anhydrous conditions. In this report, an air-stable two-component NHC photogenerator ─ 2-isopropylthioxanthone (ITX) as photosensitive species and 1,3-bis(mesityl)imidazolium tetraphenylborate (IMesH<sup>+</sup> BPh<sub>4</sub><sup>-</sup>) acting as NHC protected precursor ─ has been utilized to organocatalyze thiol-Michael reaction for small molecule and polymer synthesis. The feasibility of photoNHC catalysis in addition reactions involving thiol and ene molecules was investigated using <sup>1</sup>H NMR spectroscopy. The synthesis of cross-linked polythioether polymer via a step-growth polymerization was then studied using FTIR spectroscopy, optical pyrometry and gel content measurements.<b></b></p>

Highly Efficient Michael Reactions of Nitroolefins by Grinding Means

2019 ◽  
Vol 16 (3) ◽  
pp. 449-457 ◽  
Author(s):  
Dong-Xiao Cui ◽  
Yue-Dan Li ◽  
Jun-Chao Zhu ◽  
Yan-Yan Jia ◽  
Ai-Dong Wen ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Room Temperature ◽  
Michael Reaction ◽  
Building Blocks ◽  
Solvent Free ◽  
Michael Additions ◽  
Highly Efficient ◽  
Michael Reactions ◽  
Michael Adducts ◽  
Solvent Free Conditions

Aim and Objective: The direct β-functionalization of trans-β-nitroolefins by Michael reaction is regarded as an efficient way to provide precursors for β-functional amines. However, Michael additions by grinding means with solvent-free conditons are rarely reported. We have developed facile access to β-functional nitroalkanes by grinding means under solvent-free conditions. Materials and Methods: From commercially available materials including ethyl 2-nitroacetate, alkyl 2-cyanoacetates and malononitrile, the grinding reactions between these above-mentioned activated methylenecompounds and various trans-β-nitroolefins were performed at room temperature and solvent-free conditions. Results: A highly efficient direct Michael reaction of nitroolefins by simple grinding means has been developed. Various trans-nitrostyrenes were easily converted into corresponding β-functional nitroalkanes in excellent yields within 5~10 min (up to 36 examples). Conclusion: Herein, we have developed a simple and efficient way to β-functional nitroalkanes through Michael reactions by grinding means. The grinding Michael reaction is fast, clean and stable and these Michael adducts could be easily converted into the other amino compounds served as building blocks in organic synthesis.

Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and α,β-unsaturated ketones

2019 ◽  
Vol 17 (42) ◽  
pp. 9305-9312 ◽  
Author(s):  
Min Lu ◽  
Hong Li ◽  
Chuncheng Zou ◽  
Jianchang Li ◽  
Chengyu Liu ◽  
...  
Keyword(s):  
Primary Amine ◽  
Michael Reaction ◽  
Unsaturated Ketones ◽  
Michael Reactions ◽  
Amine Catalysts

Organocatalytic asymmetric Michael reactions between thiazolones and α,β-unsaturated ketones were developed. By using primary amine catalysts, the products were obtained with good to excellent yields and stereoselectivities.

Recent advances in the asymmetric synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-Michael reactions

2019 ◽  
Vol 17 (15) ◽  
pp. 3670-3708 ◽  
Author(s):  
Maxim G. Vinogradov ◽  
Olga V. Turova ◽  
Sergei G. Zlotin
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Nitrogen Heterocycles ◽  
Michael Reactions ◽  
Naturally Occurring ◽  
Recent Advances

In this review, recent applications of a stereoselective aza-Michael reaction for asymmetric synthesis of naturally occurring N-containing heterocyclic scaffolds and their usefulness to pharmacology are summarized.

scholarly journals Accessing HIV-1 Protease Inhibitors through Visible-Light-Mediated Sequential Photocatalytic Decarboxylative Radical Conjugate Addition-Elimination–Oxa-Michael Reactions

2021 ◽  
Author(s):  
Tomislav Krolo ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Protease Inhibitors ◽  
Carboxylic Acids ◽  
Michael Reaction ◽  
Conjugate Addition ◽  
Cyclic Ether ◽  
Synthetic Route ◽  
Michael Reactions ◽  
Synthetic Strategy ◽  
Hiv 1

A novel photocatalytic decarboxylative radical conjugate addition-elimination-oxa-Michael reaction of hydroxyalkylated carboxylic acids with cyclopentenones has been developed to construct diverse cyclopentanonyl-fused functionalized cyclic ether derivatives in the presence of an inexpensive organic photocatalyst. The stereoselective synthetic strategy is amenable to substructural variation, establishing a direct total synthetic route to two diastereomers of C3-Amino cyclopentyltetrahydrofuranyl-derived potent HIV-1 protease inhibitors with low nanomolar IC 50 values.

scholarly journals Photochemically Activated Thiol-Michael Reactions via a Photolatent N-Heterocyclic Carbene

2019 ◽  
Author(s):  
Abraham Chemtob ◽  
Bao Tram Vu Ngoc ◽  
Julien Pinaud ◽  
Patrick Lacroix-Desmazes ◽  
Valérie Héroguez
Keyword(s):  
Michael Reaction ◽  
High Sensitivity ◽  
Heterocyclic Carbenes ◽  
Addition Reactions ◽  
H Nmr ◽  
Michael Reactions ◽  
Two Component ◽  
Step Growth ◽  
Step Growth Polymerization ◽  
Spectroscopy Optical

<p>While N-heterocyclic carbenes (NHCs) have proven highly effective in various polymerization reactions, the drawback is their high sensitivity towards air and water, which necessitates handling under rigorously anhydrous conditions. In this report, an air-stable two-component NHC photogenerator ─ 2-isopropylthioxanthone (ITX) as photosensitive species and 1,3-bis(mesityl)imidazolium tetraphenylborate (IMesH<sup>+</sup> BPh<sub>4</sub><sup>-</sup>) acting as NHC protected precursor ─ has been utilized to organocatalyze thiol-Michael reaction for small molecule and polymer synthesis. The feasibility of photoNHC catalysis in addition reactions involving thiol and ene molecules was investigated using <sup>1</sup>H NMR spectroscopy. The synthesis of cross-linked polythioether polymer via a step-growth polymerization was then studied using FTIR spectroscopy, optical pyrometry and gel content measurements.<b></b></p>

Asymmetric synthesis of highly functionalized furanones via direct Michael reactions mediated by a bulky primary amine

2019 ◽  
Vol 6 (8) ◽  
pp. 1080-1083 ◽  
Author(s):  
Huicai Huang ◽  
Xue Lu ◽  
Yukang Mao ◽  
Jinxing Ye
Keyword(s):  
Asymmetric Synthesis ◽  
Primary Amine ◽  
Michael Reaction ◽  
Michael Reactions

A bulky chiral primary amine catalyzed Michael reaction of 3(2H)-furanones has been realized, leading to the construction of substituted furanone derivatives.

scholarly journals Accessing HIV-1 Protease Inhibitors through Visible-Light-Mediated Sequential Photocatalytic Decarboxylative Radical Conjugate Addition-Elimination–Oxa-Michael Reactions

2021 ◽  
Author(s):  
Tomislav Krolo ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Protease Inhibitors ◽  
Carboxylic Acids ◽  
Michael Reaction ◽  
Conjugate Addition ◽  
Cyclic Ether ◽  
Synthetic Route ◽  
Michael Reactions ◽  
Synthetic Strategy ◽  
Hiv 1

A novel photocatalytic decarboxylative radical conjugate addition-elimination-oxa-Michael reaction of hydroxyalkylated carboxylic acids with cyclopentenones has been developed to construct diverse cyclopentanonyl-fused functionalized cyclic ether derivatives in the presence of an inexpensive organic photocatalyst. The stereoselective synthetic strategy is amenable to substructural variation, establishing a direct total synthetic route to two diastereomers of C3-Amino cyclopentyltetrahydrofuranyl-derived potent HIV-1 protease inhibitors with low nanomolar IC 50 values.

Sign in / Sign up

Export Citation Format

Share Document