Organo-catalysis as emerging tools in organic synthesis: aldol and Michael reactions

2022 ◽  
Vol 0 (0) ◽  
Author(s):  
Nagaraju Kerru ◽  
Suresh Maddila ◽  
Sreekantha B. Jonnalagadda
Keyword(s):  
Organic Synthesis ◽  
Michael Addition ◽  
Addition Reactions ◽  
Chiral Molecules ◽  
Asymmetric Aldol ◽  
Bond Forming ◽  
Michael Reactions ◽  
Stereogenic Centers ◽  
Synthetic Hybrids ◽  
The Impact

Abstract Organocatalysis has occupied sustainable position in organic synthesis as a powerful tool for the synthesis of enantiomeric-rich compounds with multiple stereogenic centers. Among the various organic molecules for organocatalysis, the formation of carbon–carbon is viewed as a challenging issue in organic synthesis. The asymmetric aldol and Michael addition reactions are the most significant methods for C–C bond forming reactions. These protocols deliver a valuable path to access chiral molecules, which are useful synthetic hybrids in biologically potent candidates and desirable versatile pharmaceutical intermediates. This work highlighted the impact of organocatalytic aldol and Michael addition reactions in abundant solvent media. It focused on the crucial methods to construct valuable molecules with high enantio- and diastereo-selectivity.

Greener Approaches to Selected Asymmetric Addition Reactions Relevant to Drug Development

2021 ◽  
Vol 25 ◽  
Author(s):  
Girija S. Singh
Keyword(s):  
Aqueous Media ◽  
Solvent Free ◽  
Aldol Reactions ◽  
Addition Reactions ◽  
Asymmetric Addition ◽  
Asymmetric Aldol ◽  
Bond Forming ◽  
Michael Reactions ◽  
Carbon Carbon Bond ◽  
Solvent Free Conditions

: Asymmetric organic synthesis is of paramount importance in the development of drugs. Asymmetric addition reactions such as aldol reaction, Michael addition, and Mannich addition reactions are important carbon-carbon bond-forming reactions and have been employed in the synthesis of a broad range of biologically important molecules. Many of these reactions have been developed under solvent-free conditions or in greener solvents like water. Several reactions have been developed at room temperature or by using a non-conventional energy source such as microwave irradiation. Several greener catalysts have been developed for such reactions. The present review article discusses the application of green chemistry parameters in the development of selected asymmetric addition reactions leading to biologically important molecules during the last ten years. Asymmetric aldol reactions, asymmetric Michael reactions, and different asymmetric addition reactions involving imines such as Mannich reaction, aza-benzoin reaction, etc. in aqueous media or under solvent-free conditions have been reviewed. Application of different types of catalysts such as prolinamides, 1,2-diamines, polymer and magnetic nanoparticle-supported chiral catalysts is demonstrated.

scholarly journals Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

2017 ◽  
Vol 13 ◽  
pp. 2214-2234 ◽  
Author(s):  
Yaroslav Dmitrievich Boyko ◽  
Valentin Sergeevich Dorokhov ◽  
Alexey Yu Sukhorukov ◽  
Sema Leibovich Ioffe
Keyword(s):  
Total Synthesis ◽  
Organic Synthesis ◽  
Michael Addition ◽  
High Reactivity ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Recent Developments ◽  
Michael Acceptors

Despite of their chemical instability and high reactivity, conjugated nitrosoalkenes are useful intermediates in target-oriented organic synthesis. The present review deals with carbon–carbon bond forming reactions involving Michael addition to α-nitrosoalkenes with a particular focus on recent developments in this methodology and its use in total synthesis.

Ultrafast and efficient aza- and thiol-Michael reactions on a polyester scaffold with internal electron deficient triple bonds

2018 ◽  
Vol 9 (22) ◽  
pp. 3037-3054 ◽  
Author(s):  
Ufuk Saim Gunay ◽  
Muge Cetin ◽  
Ozgun Daglar ◽  
Gurkan Hizal ◽  
Umit Tunca ◽  
...  
Keyword(s):  
Michael Addition ◽  
Main Chain ◽  
Addition Reactions ◽  
Triple Bonds ◽  
Michael Reactions ◽  
Internal Electron

A polyester scaffold possessing electron deficient triple bonds in the main chain was prepared and utilized as a precursor for aza- and thiol-Michael addition reactions.

Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates

2017 ◽  
Vol 15 (2) ◽  
pp. 311-315 ◽  
Author(s):  
Lijun Zhang ◽  
Wenzhong Zhang ◽  
Haibo Mei ◽  
Jianlin Han ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Aldol Reactions ◽  
Addition Reactions ◽  
Asymmetric Aldol ◽  
Wide Range ◽  
Stereogenic Centers ◽  
New Type ◽  
Catalytic Asymmetric ◽  
Aldol Addition ◽  
Quaternary Stereogenic Centers

Cu(i)/bisoxazoline ligand catalyzed asymmetric aldol reactions of fluoro-indolinone derived new type tertiary enolates have been developed. This process allows the preparation of a wide range of α-fluoro-β-aryl/hetaryl/alkyl-β-hydroxy-indolin-2-one products containing C–F quaternary stereogenic centers.

Recent Developments in Highly Stereoselective Michael Addition Reactions Catalyzed by Metal Complexes

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 781-795 ◽  
Author(s):  
Alexander N. Reznikov ◽  
Yuri N. Klimochkin
Keyword(s):  
Transition Metal ◽  
Michael Addition ◽  
Rapid Development ◽  
Short Review ◽  
Cascade Reactions ◽  
Addition Reactions ◽  
Asymmetric Catalytic ◽  
Michael Reactions ◽  
Recent Developments ◽  
Metal Catalyzed

Achieving high enantioselectivity and diastereoselectivity simultaneously­ is a rather challenging task for asymmetric catalytic synthesis­. Thanks to the rapid development of asymmetric transition-metal catalysis, significant progress has been made during recent years in achieving highly enantio- and diastereoselective conjugate addition reactions with a diverse combination of Michael donors and acceptors. This short review surveys the advances in transition-metal-catalyzed asymmetric diastereoselective Michael addition including diastereodivergent catalysis developed between 2015 and 2019. The review is divided into multiple parts according to the type of nucleophiles involved in the reaction.1 Introduction2 Addition of Functionalized Ketones and Dicarbonyl Compounds3 Addition of Aldimino Esters and Their Cyclic Analogues4 Addition of Indolin-2-ones5 Vinylogous Michael Reactions6 Other Michael Donors7 Cascade Reactions Initiated by Michael Addition8 Conclusion

Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol Reactions: A Review

2022 ◽  
Vol 09 ◽  
Author(s):  
Rubina Shajahan ◽  
Rithwik Sarang ◽  
Anas Saithalavi
Keyword(s):  
Organic Synthesis ◽  
Aldol Reaction ◽  
Enantioselective Synthesis ◽  
Aldol Reactions ◽  
Reaction Conditions ◽  
Asymmetric Aldol ◽  
Bond Forming ◽  
Recent Developments ◽  
Potential Benefits ◽  
Polymer Supported

The use of proline-based organocatalysts has acquired significant importance in organic synthesis, especially in enantioselective synthesis. Proline and its derivatives are proven to be quite effective chiral organocatalysts for a variety of transformations including the aldol reaction, which is considered as one of the important C-C bond forming reactions in organic synthesis. The use of chiral organocatalysts has several advantages over its metal-mediated analogues. Subsequently, a large number of highly efficient proline-based organocatalysts including polymer-supported chiral analogues have been identified for aldol reaction. The use of polymer-supported organocatalysts exhibited remarkable stability under the reaction conditions and offered the best results particularly in terms of its recyclability and reusability. These potential benefits along with its economic and green chemistry advantages have led to the search for many polymer-supported proline catalysts. In this review, recent developments in exploring various polymer immobilized proline-based chiral organocatalysts for asymmetric aldol reactions are described.

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