scholarly journals Step economy in the Stereoselective Synthesis of Functionalized Oxindoles via Organocatalytic Domino/One-pot Reactions

2021 ◽  
Vol 25 ◽  
Author(s):  
Martina Bortolami ◽  
Francesca Leonelli ◽  
Marta Feroci ◽  
Fabrizio Vetica
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Stereoselective Synthesis ◽  
Environmentally Friendly ◽  
Important Class ◽  
One Pot ◽  
Asymmetric Organocatalysis ◽  
Toxic Approach

: Oxindoles are an important class of heterocyclic scaffolds widely present in natural products and bioactive compounds. For this reason, a plethora of methodologies for the stereoselective synthesis of enantioenriched oxindoles has been studied over the years. Among all the reported synthetic strategies, organocatalysis has proven to be a powerful tool for the asymmetric synthesis of this class of compounds being a step- and atom-economical, environmentally friendly, and non-toxic approach. This review will outline the application of asymmetric organocatalysis in the synthesis of chiral oxindole-based structures, relying on domino/one-pot reaction sequences in a step-economical fashion.

Enantioselective Vinylogous Reactions of 3-Alkylidene Oxindoles

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2463-2472 ◽  
Author(s):  
Renato Dalpozzo ◽  
Raffaella Mancuso
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Carbonyl Compounds ◽  
Important Class ◽  
Chiral Molecules ◽  
Research Groups ◽  
Mannich Reactions ◽  
The Creation ◽  
Synthetic Derivatives

Oxindoles represent an important class of bioactive compounds and synthetic derivatives found in many natural products. Most of these compounds are chiral molecules and the challenge of their asymmetric synthesis has fascinated many research groups. In particular, the creation of chiral centers out of the oxindole ring by vinylogous addition to 3-alkylidene-substituted oxindoles (3-alkylidene-1,3-dihydro-2H-indol-2-ones) has emerged in recent years. This review aims to give an overview of this topic.1 Introduction2 Aldol and Mannich Reactions3 Addition to Unsaturated Carbonyl Compounds4 Addition to Nitroalkenes5 Miscellaneous6 Conclusion

Glucose - and Allose-Derived Chiral Auxiliaries

2019 ◽  
Vol 800 ◽  
pp. 36-41
Author(s):  
Evija Rolava ◽  
Jevgeņija Lugiņina ◽  
Māris Turks
Keyword(s):  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Important Class ◽  
Chiral Auxiliaries ◽  
Asymmetric Alkylation ◽  
Pharmaceutical Agents

Oxazolidinones are an important class of heterocyclic compounds that are used as chiral auxiliaries in asymmetric synthesis and as biologically active pharmaceutical agents. Moreover, carbohydrates are ideal scaffolds to generate libraries of bioactive compounds due the presence of defined configuration. We report here asymmetric alkylation studies on N-derivatized glucose-and allose-based spirooxazolidinones which do act as chiral auxiliaries.

Asymmetric Organocatalytic Syntheses of Bioactive Compounds

2021 ◽  
Vol 18 ◽  
Author(s):  
Estibaliz Sansinenea ◽  
Aurelio Ortiz
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Cascade Reactions ◽  
Biologically Active ◽  
Active Compounds ◽  
Total Syntheses ◽  
Main Structure ◽  
New Methodologies ◽  
High Stereoselectivity

Background: The total syntheses of complex natural products have evolved to include new methodologies to save time, simplifying the form to achieve these natural compounds. Objective: In this review, we have described the asymmetric synthesis of different natural products and biologically active compounds of the last ten years until the current day. Results: An asymmetric organocatalytic reaction is the key to generate stereoselectively the main structure with the required stereochemistry. Conclusion: Even more remarkable, the organocatalytic cascade reactions, which are carried out with high stereoselectivity, as well as a possible approximation of the organocatalysts activation with substrates are also described.

A Mini-Review: Achievements in the Thiolysis of Epoxides

2020 ◽  
Vol 17 (4) ◽  
pp. 352-362 ◽  
Author(s):  
Zhihua Chen ◽  
Saeed Mohammadi Nasr ◽  
Mosstafa Kazemi ◽  
Masoud Mohammadi
Keyword(s):  
Natural Products ◽  
Bioactive Compounds ◽  
Ring Opening ◽  
Solvent Free ◽  
Organosulfur Compounds ◽  
Important Class ◽  
Research Groups ◽  
Diverse Range ◽  
Solvent Free Conditions ◽  
Ring Opening Reactions

The β-hydroxy sulfides are an important class of organosulfur compounds that have a key role in the synthesis of bioactive compounds containing biological and natural products. The thiolysis of epoxides is the most common and best route for the synthesis of β-hydroxy sulfides. During the last decade, the applications of a diverse range of catalysts and promoter agents in green and organic mediums as well as under solvent-free conditions for the regioselective ring-opening reactions of epoxides with thiols in order to synthesize β-hydroxy sulfides have been studied by various research groups. This review is focused on the important achievements reported in the literature for the thiolysis of epoxides.

Asymmetric synthesis of 3,3′-pyrrolidinyl-dispirooxindoles via a one-pot organocatalytic Mannich/deprotection/aza-Michael sequence

2016 ◽  
Vol 52 (11) ◽  
pp. 2249-2252 ◽  
Author(s):  
Kun Zhao ◽  
Ying Zhi ◽  
Xinyi Li ◽  
Rakesh Puttreddy ◽  
Kari Rissanen ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Stereoselective Synthesis ◽  
One Pot ◽  
Stereogenic Centers

A highly stereoselective synthesis of functionalized 3,3′-pyrrolidinyl-dispirooxindole derivatives with three stereogenic centers, including two contiguous spiro-stereocenters, has been achieved through an organocatalytic Mannich/Boc-deprotection/aza-Michael sequence.

Multicomponent Reactions in the Synthesis of Complex Fused Coumarin Derivatives

2018 ◽  
Vol 15 (1) ◽  
pp. 21-37 ◽  
Author(s):  
Ligia S. da Silveira Pinto ◽  
Mara R.C. Couri ◽  
Marcus V.N. de Souza
Keyword(s):  
Natural Products ◽  
Green Chemistry ◽  
Multicomponent Reactions ◽  
High Selectivity ◽  
Complex Compounds ◽  
Important Class ◽  
Coumarin Derivatives ◽  
One Pot

Background: Coumarin is an important class of natural products with applications in different areas of knowledge. Due to its importance, several methodologies and strategies have been developed for the synthesis of different classes of compounds containing this nucleus. Objective: The aim of this review is to cover in the last five years the complex fused coumarin derivatives synthesized in one-pot three-component reactions. Conclusion: Considering that multicomponent reactions are a powerful tool to produce simple and complex compounds in one or few steps with high selectivity and yields while following the green chemistry principles.

Asymmetric Synthesis of Natural Products and Medicinal Drugs through One-Pot-Reaction Strategies

Synthesis ◽  
2015 ◽  
Vol 47 (21) ◽  
pp. 3257-3285 ◽  
Author(s):  
Bor-Cherng Hong ◽  
Arun Raja ◽  
Vishal Sheth
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
One Pot ◽  
Medicinal Drugs

scholarly journals Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1308
Author(s):  
Alejandro Manchado ◽  
Victoria Elena Ramos ◽  
David Díez ◽  
Narciso M. Garrido
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Asymmetric Synthesis ◽  
Heteronuclear Nmr ◽  
Domino Reaction ◽  
One Pot ◽  
Pharmaceutical Development ◽  
New Drug ◽  
Anti Inflammatory ◽  
Pharmaceutical Properties

The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development.

scholarly journals Asymmetric Synthesis of Tetrahydroisoquinoline Alkaloids Using Ellman's Chiral Auxiliary

2017 ◽  
Vol 12 (10) ◽  
pp. 1934578X1701201
Author(s):  
Y. Vikram Reddy ◽  
Dhanraj O. Biradar ◽  
B. Jagan Mohan Reddy ◽  
Aravinda Rathod ◽  
M. Himabindu ◽  
...  
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Stereoselective Synthesis ◽  
Chiral Auxiliary ◽  
First Report

Chiral t-butylsulfinamide has been successfully employed for the stereoselective synthesis of 1-benzyl tetrahydroisoquinoline alkaloids. This is the first report on the synthesis of chiral 1-benzyltetrahydroisoquinoline natural products using tert-butylsulfinamide through a haloamide cyclization.

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