Recent Advances in the Synthesis and Chemistry of Nitronates

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3255-3268 ◽  
Author(s):  
Andrey Tabolin ◽  
Alexey Sukhorukov ◽  
Sema Ioffe ◽  
Alexander Dilman

Due to their availability and versatile reactivity, nitronates have become important building blocks in the stereoselective synthesis of bioactive molecules. This short review provides a summary of recent developments on the synthesis, chemistry and applications of O-alkyl and O-silyl nitronates.1 Introduction2 Approaches to the Synthesis of Nitronates2.1 Synthesis of Six-Membered Cyclic Nitronates2.1.1 Formal [4+2] Approaches2.1.2 Formal [3+3] Approaches2.1.3 Other Approaches2.2 Synthesis of Five-Membered Cyclic Nitronates2.2.1 Formal [3+2] Approaches2.2.2 Formal [4+1] Approaches2.2.3 Oxidation Approaches3 Chemistry of Nitronates3.1 Nitronates as α-C-Nucleophiles3.2 Nitronates as α-C-Electrophiles3.3 Nitronates in [3+n]-Annulation Reactions3.4 Reactions Involving the β-Carbon Atom of Nitronates3.5 Miscellaneous Transformations4 Conclusion

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4906
Author(s):  
Jurriën W. Collet ◽  
Thomas R. Roose ◽  
Bram Weijers ◽  
Bert U. W. Maes ◽  
Eelco Ruijter ◽  
...  

Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.


Author(s):  
Sonali Jana ◽  
Piyali Das ◽  
Joydeep Mukherjee ◽  
Dipak Banerjee ◽  
Prabal Ranjan Ghosh ◽  
...  

Recent developments in the biomedical arena have led to the progress of several biomaterials by utilizing bioactive molecules from biological wastes arising from the fish, meat, and poultry industries. These...


Author(s):  
Min Zhang ◽  
Ying Gong ◽  
Wei Zhou ◽  
Ying Zhou ◽  
Xiong-Li Liu

Chiral polycyclic chromanones are important heterocyclic frameworks that constitute the core structures of many natural products and bioactive molecules. As starting materials, the chromone-based reactants are very efficient building blocks...


Synthesis ◽  
2020 ◽  
Author(s):  
Shiyong Peng ◽  
Nuan Chen ◽  
Min He ◽  
Ting Zhou ◽  
Yuqi Zhu ◽  
...  

AbstractThis short review summarizes the most recent developments (since 2010) in the tandem cyclization/cycloaddition of allene intermediates­, generated from the copper-catalyzed cross-coupling of diazo compounds with terminal alkynes, to afford cyclic compounds.1 Introduction2 Cyclization2.1 Cyclization with Nucleophiles2.2 Cyclization with Electrophiles2.3 6π-Electrocyclization2.4 Other Cyclization3 Cycloaddition4 Conclusion


Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 135-145 ◽  
Author(s):  
Naohiko Yoshikai

This Short Review describes recent developments in cobalt-catalyzed enantioselective C–C bond-forming reactions. The article focuses on reactions that most likely involve chiral organocobalt species as crucial catalytic intermediates and their mechanistic aspects.1 Introduction2 Hydrovinylation3 C–H Functionalization4 Cycloaddition and Cyclization5 Addition of Carbon Nucleophiles6 Cross-Coupling7 Conclusion


Synthesis ◽  
2021 ◽  
Author(s):  
Qing-Zhu Li ◽  
Wen-Lin Zou ◽  
Zhi-Qiang Jia ◽  
Jun-Long Li

Allyl and propargyl sulfonium salts are readily available reagents and have recently emerged as versatile building blocks in the assembly of cyclic skeletons. As an alternative to the classical sulfonium salts, allyl and propargyl sulfonium salts can convert to the corresponding vinyl sulfur ylide or allenic sulfonium salt intermediates that contain diverse nucleophilic or electrophilic reactive positions, thereby enabling a great variety of annulation reactions. In this review, we provide a comprehensive overview of the recent developments on this growing field by summarizing the annulation reactions involving allyl and propargyl sulfonium salts.


2015 ◽  
Vol 11 ◽  
pp. 2278-2288 ◽  
Author(s):  
Kirk W Shimkin ◽  
Donald A Watson

Recently, a number of papers have emerged demonstrating copper-catalyzed alkylation reactions of electron-rich small molecules. The processes are generally thought to be related to long established atom-transfer radical reactions. However, unlike classical reactions, these new transformations lead to simple alkylation products. This short review will highlight recent advances in alkylations of nitronate anions, alkenes and alkynes, as well as discuss current mechanistic understanding of these novel reactions.


Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3337-3346 ◽  
Author(s):  
Manabu Abe ◽  
Youhei Chitose ◽  
Satish Jakkampudi ◽  
Pham Thuy ◽  
Qianghua Lin ◽  
...  

Near-infrared two-photon (TP)-induced photorelease (uncaging) of bioactive molecules such as drugs has attracted considerable attention because of its ability to elucidate mechanistic aspects of biological processes. This short review summarizes recent developments in the design and synthesis of TP-responsive chromophores.1 Introduction2 Molecular Design of TP-Responsive Organic Chromophores for ‘Caging & Uncaging’2.1 π-Conjugation2.2 A Dipolar System2.3 A Quadrupolar System2.4 An Octupolar System3 Recent Developments of TP Uncaging Reactions3.1 4-Methoxy-7-nitroindolinyl Caged Auxins3.2 Uncaging of GABA and Tryptophan Using TP-Induced Electron-Transfer Reactions3.3 Effect of Position Isomery in Aminoquinoline-Derived Photolabile Protecting Groups (PPGs)3.4 Cooperative Dyads for TP Uncaging3.5 Caged Calcium with a Bis-styrylthiophene Backbone3.6 Cloaked Caged Compounds3.7 Three-Dimensional Control of DNA Hybridization by Orthogonal Two-Color TP Uncaging3.8 TP-Induced Release of Diethyl Phosphate (DEP) and ATP4 Our Contribution to TP Uncaging Reactions5 Summary


Synthesis ◽  
2021 ◽  
Author(s):  
Biwei Yan ◽  
Wusheng Guo

Functionalized cyclic organic carbonates have emerged as valuable building blocks for the construction of interesting and useful molecules upon decarboxylation under transition metal catalysis in recent years. With suitable catalytic system, the development of chemo-, regio-, stereo- and enantioselective methods for the synthesis of useful and interesting compounds has advanced greatly. On the basis of previous research work on this topic, this short review will highlight the synthetic potential of cyclic carbonates under transition metal catalysis in last two years. 1 Introduction 2 Transition metal catalyzed decarboxylation of vinyl cyclic carbonates 3 Zwitterionic enolate chemistry based on transition metal catalysis 4 Decarboxylation of alkynyl cyclic carbonates and dioxazolones 5 Conclusions and perspectives


2011 ◽  
Vol 64 (5) ◽  
pp. 519 ◽  
Author(s):  
Zhe Sun ◽  
Jishan Wu

Higher order acenes and fused acenes represent two outstanding classes of building blocks to achieve near-infrared absorbing and emitting materials. Appropriate chemical modification and functionalization will lead to significant improvements in solubility and stability, thus making their applications practically possible. This short review summarizes the recent developments of the two types of polycyclic aromatic compounds mentioned above based on their physical and optical properties including absorption, emission, quantum yield, solubility, and stability.


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