scholarly journals Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

2020 ◽  
Vol 16 ◽  
pp. 212-232 ◽  
Author(s):  
Delphine Pichon ◽  
Jennifer Morvan ◽  
Christophe Crévisy ◽  
Marc Mauduit
Keyword(s):  
Natural Products ◽  
Conjugate Addition ◽  
Catalytic Transformation ◽  
Chiral Molecules ◽  
Catalytic Systems ◽  
Organometallic Reagents ◽  
Recent Advances ◽  
Wide Range ◽  
Michael Acceptors

The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic nucleophiles to electron-deficient alkenes (Michael acceptors) represents an efficient and attractive methodology for providing a wide range of relevant chiral molecules. In order to increase the attractiveness of this useful catalytic transformation, some Michael acceptors bearing challenging electron-deficient functions (i.e., aldehydes, thioesters, acylimidazoles, N-acyloxazolidinones, N-acylpyrrolidinones, amides, N-acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic systems have successfully achieved the conjugate addition of different organometallic reagents to these challenging Michael acceptors, with excellent regio- and enantioselectivity. Furthermore, thanks to their easy derivatization, the resulting chiral conjugated products could be converted into various natural products. The aim of this tutorial review is to summarize recent advances accomplished in this stimulating field.

scholarly journals Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

2015 ◽  
Vol 11 ◽  
pp. 2418-2434 ◽  
Author(s):  
Thibault E Schmid ◽  
Sammy Drissi-Amraoui ◽  
Christophe Crévisy ◽  
Olivier Baslé ◽  
Marc Mauduit
Keyword(s):  
Conjugate Addition ◽  
Chiral Molecules ◽  
Straightforward Manner ◽  
Organometallic Reagents ◽  
Stereogenic Centers ◽  
Michael Acceptors ◽  
Sequential Generation

The copper-catalyzed asymmetric conjugate addition (ACA) of nucleophiles onto polyenic Michael acceptors represents an attractive and powerful methodology for the synthesis of relevant chiral molecules, as it enables in a straightforward manner the sequential generation of two or more stereogenic centers. In the last decade, various chiral copper-based catalysts were evaluated in combination with different nucleophiles and Michael acceptors, and have unambiguously demonstrated their usefulness in the control of the regio- and enantioselectivity of the addition. The aim of this review is to report recent breakthroughs achieved in this challenging field.

ChemInform Abstract: Copper-Catalyzed Asymmetric Conjugate Addition of Organometallic Reagents to Extended Michael Acceptors

ChemInform ◽  
2016 ◽  
Vol 47 (12) ◽  
pp. no-no
Author(s):  
Thibault E. Schmid ◽  
Sammy Drissi-Amraoui ◽  
Christophe Crevisy ◽  
Olivier Basle ◽  
Marc Mauduit
Keyword(s):  
Conjugate Addition ◽  
Organometallic Reagents ◽  
Michael Acceptors

Chiral Amine-Mediated Asymmetric Conjugate Additions to Vinyl Sulfones

2009 ◽  
Vol 62 (9) ◽  
pp. 951 ◽  
Author(s):  
Qiang Zhu ◽  
Yixin Lu
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Conjugate Addition ◽  
Chiral Molecules ◽  
Conjugate Additions ◽  
Chiral Amine ◽  
Michael Acceptors

Chiral molecules containing sulfone groups are useful intermediates and have found wide applications in organic synthesis. In this account, recent progress in the use of vinyl sulfones as Michael acceptors in the asymmetric organocatalytic conjugate addition is summarized.

Recent Advances in the Hofmann Rearrangement and Its Application to Natural Product Synthesis

2020 ◽  
Vol 23 (22) ◽  
pp. 2402-2435
Author(s):  
Pradip Debnath
Keyword(s):  
Natural Products ◽  
Natural Product Synthesis ◽  
Biologically Active ◽  
Primary Amines ◽  
Hypervalent Iodine ◽  
Catalytic Systems ◽  
Waste Products ◽  
Factors Affecting ◽  
Hofmann Rearrangement ◽  
Recent Advances

: C-N bond formation reactions are the most important transformations in (bio)organic chemistry because of the widespread occurrence of amines in pharmaceuticals, natural products, and biologically active compounds. The Hofmann rearrangement is a well-known method used for the preparation of primary amines from amides. But, the traditional version of the Hofmann rearrangement often gave relatively poor yields due to over-oxidation or due to the poor solubility of some amides in aqueous base, and created an enormous amount of waste products. Developments over the last two decades, in particular, have focused on refining both of these factors affecting the reaction. This review covers both the description of recent advances (2000-2019) in the Hofmann rearrangements and its applications in the synthesis of heterocycles, natural products and complex molecules of biological interest. It is revealed that organo-catalytic systems especially hypervalent iodine-based catalysts have been developed for the green and environmentally friendly conversion of carboxamides to primary amines and carbamates.

Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3818-3836
Author(s):  
Jin-Heng Li ◽  
De-Lie An ◽  
Jing-Hao Qin
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reactions ◽  
Structural Motifs ◽  
Recent Advances ◽  
Wide Range ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.1 Introduction2 Intermolecular Cycloaddition To Construct Azepine Derivatives2.1 [5+2] Cycloaddition2.2 [3+2+2] Cycloaddition2.3 [3+2]/[5+2] Cycloaddition3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins4 Intermolecular [3+2] Cycloaddition To Construct Spirohetero­cyclic Compounds, Indoles, Furans, and Pyrroles5 Summary and Outlook

Recent advances in the use of catalysts based on natural products for the conversion of CO2 into cyclic carbonates

2020 ◽  
Vol 22 (22) ◽  
pp. 7665-7706 ◽  
Author(s):  
Carmen Claver ◽  
Md Bin Yeamin ◽  
Mar Reguero ◽  
Anna M. Masdeu-Bultó
Keyword(s):  
Carbon Dioxide ◽  
Natural Products ◽  
Natural Product ◽  
Cyclic Carbonates ◽  
Catalytic Systems ◽  
Recent Advances

In this review we present a structured overview of the chemical catalytic systems containing any component derived from a natural product for the cycloaddition of carbon dioxide to epoxides to form cyclic carbonates.

Recent advances in Michael addition of H-phosphonates

RSC Advances ◽  
2014 ◽  
Vol 4 (49) ◽  
pp. 26002-26012 ◽  
Author(s):  
A. Yu. Rulev
Keyword(s):  
Michael Addition ◽  
Environmentally Friendly ◽  
Conjugate Addition ◽  
Recent Advances ◽  
Michael Acceptors

The review discusses recent achievements in the development of more environmentally friendly and economically competitive processes for the synthesis of biologically and synthetically important phosphorus-bearing compounds by conjugate addition of hydrogen-phosphonates to different Michael acceptors.

scholarly journals Recent Advances in Enzymatic and Non-Enzymatic Electrochemical Glucose Sensing

Sensors ◽  
2021 ◽  
Vol 21 (14) ◽  
pp. 4672
Author(s):  
Mohamed H. Hassan ◽  
Cian Vyas ◽  
Bruce Grieve ◽  
Paulo Bartolo
Keyword(s):  
Noble Metals ◽  
Direct Electrochemistry ◽  
Glucose Sensing ◽  
Glucose Sensors ◽  
Diabetic Patients ◽  
Past Century ◽  
Industrial Sectors ◽  
Recent Advances ◽  
Wide Range ◽  
Sensitivity And Selectivity

The detection of glucose is crucial in the management of diabetes and other medical conditions but also crucial in a wide range of industries such as food and beverages. The development of glucose sensors in the past century has allowed diabetic patients to effectively manage their disease and has saved lives. First-generation glucose sensors have considerable limitations in sensitivity and selectivity which has spurred the development of more advanced approaches for both the medical and industrial sectors. The wide range of application areas has resulted in a range of materials and fabrication techniques to produce novel glucose sensors that have higher sensitivity and selectivity, lower cost, and are simpler to use. A major focus has been on the development of enzymatic electrochemical sensors, typically using glucose oxidase. However, non-enzymatic approaches using direct electrochemistry of glucose on noble metals are now a viable approach in glucose biosensor design. This review discusses the mechanisms of electrochemical glucose sensing with a focus on the different generations of enzymatic-based sensors, their recent advances, and provides an overview of the next generation of non-enzymatic sensors. Advancements in manufacturing techniques and materials are key in propelling the field of glucose sensing, however, significant limitations remain which are highlighted in this review and requires addressing to obtain a more stable, sensitive, selective, cost efficient, and real-time glucose sensor.

Chiral imidazolidinones: A class of priviliged organocatalysts in stereoselective organic synthesis

2020 ◽  
Vol 5 (5) ◽  
Author(s):  
Laura Raimondi ◽  
Chiara Faverio ◽  
Monica Fiorenza Boselli
Keyword(s):  
Pharmaceutical Industry ◽  
Green Chemistry ◽  
Organic Synthesis ◽  
Catalytic Synthesis ◽  
Biological Chemistry ◽  
Chiral Molecules ◽  
Catalytic Systems ◽  
Drug Synthesis ◽  
Industry Needs

AbstractChiral molecules hold a mail position in Organic and Biological Chemistry, so pharmaceutical industry needs suitable strategies for drug synthesis. Moreover, Green Chemistry procedures are increasingly required in order to avoid environment deterioration. Catalytic synthesis, in particular organocatalysis, in thus a continuously expanding field. A survey of more recent researches involving chiral imidazolidinones is here presented, with a particular focus on immobilized catalytic systems.

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