scholarly journals Organocatalytic Name Reactions Enabled by NHCs

Materials ◽  
2020 ◽  
Vol 13 (16) ◽  
pp. 3574
Author(s):  
Krzysztof Dzieszkowski ◽  
Izabela Barańska ◽  
Karina Mroczyńska ◽  
Michał Słotwiński ◽  
Zbigniew Rafiński
Keyword(s):  
Organic Chemistry ◽  
Total Synthesis ◽  
Heterocyclic Carbenes ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Great Opportunity

Giving reactions the names of their discoverers is an extraordinary tradition of organic chemistry. Nowadays, this phenomenon is much rarer, although already named historical reactions are still often developed. This is also true in the case of a broad branch of N‑heterocyclic carbenes catalysis. NHCs allow many unique synthetic paths, including commonly known name reactions. This article aims to gather this extensive knowledge and compare historical reactions with current developed processes. Furthermore, this review is a great opportunity to highlight some of the unique applications of these procedures in the total synthesis of biologically active compounds. Hence, this concise article may also be a source of knowledge for scientists just starting their adventure with N‑heterocyclic carbene chemistry.

scholarly journals Tale of Breslow Intermediate, a Central Player in N-Heterocyclic Carbene Organocatalysis: Then and Now

2021 ◽  
Author(s):  
Raghavan B. Sunoj ◽  
Monika Pareek ◽  
Yernaidu Reddi
Keyword(s):  
Natural Products ◽  
Heterocyclic Carbenes ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Wide Range

N-heterocyclic carbenes (NHCs) belong to the popular family of organocatalysts used in a wide range of reactions, including that for the synthesis of complex natural products and biologically active compounds....

Stereoselective strategies for the construction of polysubstituted piperidinic compounds and their applications in natural products’ synthesis

2017 ◽  
Vol 4 (8) ◽  
pp. 1655-1704 ◽  
Author(s):  
Nishanth Kandepedu ◽  
Isabelle Abrunhosa-Thomas ◽  
Yves Troin
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Natural Products Synthesis

An abridged and far-reaching review communication on the construction of the polysubstituted piperidinic core using diverse methodologies for the benefit of organic chemists interested in the total synthesis of biologically active compounds.

scholarly journals 1,3-Cyclohexadien-1-Als: Synthesis, Reactivity and Bioactivities

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1772
Author(s):  
Ignacio E. Tobal ◽  
Rocío Bautista ◽  
David Diez ◽  
Narciso M. Garrido ◽  
Pilar García-García
Keyword(s):  
Organic Chemistry ◽  
Building Block ◽  
Building Blocks ◽  
Natural Compounds ◽  
Diels Alder ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Complex Molecules ◽  
Active Compounds ◽  
Electron Withdrawing Group

In synthetic organic chemistry, there are very useful basic compounds known as building blocks. One of the main reactions wherein they are applied for the synthesis of complex molecules is the Diels–Alder cycloaddition. This reaction is between a diene and a dienophile. Among the most important dienes are the cyclic dienes, as they facilitate the reaction. This review considers the synthesis and reactivity of one of these dienes with special characteristics—it is cyclic and has an electron withdrawing group. This building block has been used for the synthesis of biologically active compounds and is present in natural compounds with interesting properties.

scholarly journals Direct Synthesis of Unprotected 2-Azidoamines from Alkenes via an Iron-Catalyzed Difunctionalization Reaction

2020 ◽  
Author(s):  
Szabolcs Makai ◽  
Eric Falk ◽  
Bill Morandi
Keyword(s):  
Total Synthesis ◽  
Functional Group ◽  
Direct Synthesis ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Simple Synthesis ◽  
Active Compounds ◽  
Complex Drug ◽  
Vicinal Diamines

<div> <p>Unprotected, primary 2-azidoamines are versatile precursors to vicinal diamines, which are among the most common motifs in biologically active compounds. Herein, we report their operationally simple synthesis through an iron-catalyzed difunctionalization of alkenes. A wide array of alkene substrates are tolerated, including complex drug-like molecules and a tripeptide. Facile derivatizations of the azidoamine group demonstrate the versatility of this masked diamine motif in chemoselective, orthogonal transformations. Applications of the methodology in the concise synthesis of RO 20-1724 and in a formal total synthesis of (±)-hamacanthin B further demonstrate the broad synthetic potential of this highly functional group tolerant reaction.</p> </div>

scholarly journals Electrophilic Iodination of Organic Compounds Using Elemental Iodine or Iodides: Recent Advances 2008–2021: Part I

Compounds ◽  
2022 ◽  
Vol 2 (1) ◽  
pp. 3-24
Author(s):  
Njomza Ajvazi ◽  
Stojan Stavber
Keyword(s):  
Organic Chemistry ◽  
Organic Compounds ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Present Review ◽  
Active Compounds ◽  
Synthetic Organic Chemistry ◽  
Recent Advances ◽  
Elemental Iodine

The iodination of organic compounds is of great importance in synthetic organic chemistry. It opens comprehensive approaches for the synthesis of various biologically active compounds. The recent advances in iodination of organic compounds using elemental iodine or iodides, covering the last thirteen years, are the objective of the present review.

scholarly journals Modular Chiral N-Heterocyclic Carbene Ligands for the Nickel-Catalyzed Enantioselective C–H Functionalization of Heterocycles

2020 ◽  
Vol 74 (4) ◽  
pp. 278-284
Author(s):  
Johannes Diesel ◽  
Nicolai Cramer
Keyword(s):  
Transition Metals ◽  
Asymmetric Catalysis ◽  
Heterocyclic Carbenes ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Carbene Ligands ◽  
Active Compounds ◽  
Flexible Ligand ◽  
Mild Conditions ◽  
Bicyclic Compounds

N-Heterocyclic carbenes (NHCs) are the ligands of choice in a large variety of transformations entailing different transition metals. However, the number and variety of chiral NHCs suitable as stereo-controlling ligands in asymmetric catalysis remains limited. Herein we highlight the introduction of a modular NHC ligand family, consisting of a chiral version of the widely used IPr ligand. These chiral NHC ligands were applied in the nickel-catalyzed enantioselective C–H functionalization of N-heterocycles. Nickel-NHC catalysis unlocked the stereoselective C–H annulation of 2- and 4-pyridones, delivering fused bicyclic compounds found in many biologically active compounds. Applying a bulky, yet flexible ligand scaffold enabled the highly enantioselective C–H functionalization of pyridones under mild conditions. The introduction of a bulky chiral SIPr analogue enabled the nickel-catalyzed enantioselective C–H functionalization of indoles, yielding valuable tetrahydropyridoindoles. Additionally, pyrrolopyridines, pyrrolopyrimidines and pyrroles were efficiently functionalized, delivering chiral annulated azoles.

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