Current advances of organocatalytic Michael–Michael cascade reaction in the synthesis of highly functionalized cyclic molecules

Nayak, Smita; Panda, Pravati; Bhakta, Sujitlal; Mishra, Sambita K.; Mohapatra, Seetaram

doi:10.1039/c6ra21191g

Cited by 60 publications

(22 citation statements)

References 57 publications

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“…In this framework, Brønsteda cidc atalyzed cascadesi nvolving nitro-alkenes have been extensively used to quicklyincreasemolecular complexity startingf rom simple substrates. Notably,d ouble Michael addition sequences [18] have been used to afford, after au nique step, elaborate (poly)cyclic structures displaying multiple stereogenic centers in ao ne-pot fashion ( Figure 3).…”

Section: Double Michaeladdition Cascadementioning

confidence: 99%

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Merad

Lalli

Bernadat³

et al. 2017

Chemistry A European J

157

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Synthesis of biologically active molecules (whether at laboratory or industrial scale) remains a highly appealing area of modern organic chemistry. Nowadays, the need to access original bioactive scaffolds goes together with the desire to improve synthetic efficiency, while reducing the environmental footprint of chemical activities. Long neglected in the field of total synthesis, enantioselective organocatalysis has recently emerged as an environmentally friendly and indispensable tool for the construction of relevant bioactive molecules. Notably, enantioselective Brønsted acid catalysis has offered new opportunities in terms of both retrosynthetic disconnections and controlling stereoselectivity. The present report attempts to provide an overview of enantioselective total or formal syntheses designed around Brønsted acid-catalyzed transformations. To demonstrate the versatility of the reactions promoted and the diversity of the accessible motifs, this Minireview draws a systematic parallel between methods and retrosynthetic analysis. The manuscript is organized according to the main reaction types and the nature of newly-formed bonds.

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Section: Double Michaeladdition Cascadementioning

confidence: 99%

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Merad

Lalli

Bernadat³

et al. 2017

Chemistry A European J

157

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“…Com o advento da organocatálise e seus modos de ativação genéricos, diversas organocascatas, reações em cascata cujas etapas são organocatalisadas, foram pensadas baseando-se na ortogonalidade dos modos de ativação dos diversos substratos presentes. 121,122 Uma revisão minuciosa sobre o desenvolvimento das organocascatas está fora do escopo desta publicação, dada a complexidade do assunto, o grande número de trabalhos publicados e a diversidade das estratégias sintéticas empregadas, mas diversas revisões recentes dedicadas exclusivamente a este tema podem ser encontradas, desde as mais genéricas [120][121][122][123][124] até as mais específicas [125][126][127] sobre algum tipo particular de cascata. Uma recente publicação na área mostra a síntese enantiosseletiva de espiro-tiazol-4-onas 113 e 114 através de uma reação multicomponente, cujo mecanismo proposto pelos autores passa por três etapas em cascata (adição de Michael -adição de Michael -adição de Henry), organocatalisadas pelo derivado de esquaramida 112, promovendo sequenciais ativações por ligação de hidrogênio.…”

Section: Organocascatasunclassified

Organocatálise Enantiosseletiva: Evolução E Aspectos Recentes

Finelli

Santos

Frota

2019

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In the last two decades, enantioselective organocatalysis has established itself as one of the three pillars of asymmetric catalysis. The rapid growth in the area is due to the rationalization of organocatalysis based on the generic modes of catalyst activation, being applied to several types of reactions, in a rather generic and predictable way and providing high enantioselectivities. This tutorial review presents the evolution of this area through a brief discussion on all generic modes of activation previously systematized in the literature: activation via enamine, iminium ion, hydrogen-bonding, counterion, SOMO, photoredox, carbene and phase-transfer, and the recent advances in the area.

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“…There are several review articles available on organocatalytic asymmetric aza-MRs, each highlighting a certain aspect of the reaction. While Sánchez-Roselló et al [ 18 ] classified these reactions on the basis of the nature of the substrates, Nayak et al [ 19 ] and Bhanja et al [ 20 ] focused on the stereoselective synthesis of nitrogen heterocycles via Michael cascade reactions. Recently, Vinogradov et al [ 21 ] reviewed the synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-MRs. On the other hand, Enders et al [ 22 ], Wang et al [ 23 ] as well as Krishna et al [ 24 ] highlighted the scope and catalytic performances of some organocatalysts in asymmetric aza-MRs.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

Sharma

Bansal

2021

Beilstein J. Org. Chem.

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Nitrogen-containing scaffolds are ubiquitous in nature and constitute an important class of building blocks in organic synthesis. The asymmetric aza-Michael reaction (aza-MR) alone or in tandem with other organic reaction(s) is an important synthetic tool to form new C–N bond(s) leading to developing new libraries of diverse types of bioactive nitrogen compounds. The synthesis and application of a variety of organocatalysts for accomplishing highly useful organic syntheses without causing environmental pollution in compliance with ‘Green Chemistry” has been a landmark development in the recent past. Application of many of these organocatalysts has been extended to asymmetric aza-MR during the last two decades. The present article overviews the literature published during the last 10 years concerning the asymmetric aza-MR of amines and amides catalysed by organocatalysts. Both types of the organocatalysts, i.e., those acting through non-covalent interactions and those working through covalent bond formation have been applied for the asymmetric aza-MR. Thus, the review includes the examples wherein cinchona alkaloids, squaramides, chiral amines, phase-transfer catalysts and chiral bifunctional thioureas have been used, which activate the substrates through hydrogen bond formation. Most of these reactions are accompanied by high yields and enantiomeric excesses. On the other hand, N-heterocyclic carbenes and chiral pyrrolidine derivatives acting through covalent bond formation such as the iminium ions with the substrates have also been included. Wherever possible, a comparison has been made between the efficacies of various organocatalysts in asymmetric aza-MR.

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Current advances of organocatalytic Michael–Michael cascade reaction in the synthesis of highly functionalized cyclic molecules

Abstract: Organocatalytic domino/cascade reactions provide a convenient method for the construction of highly functionalized cyclic molecular structures bearing multiple stereocenters in a highly stereoselective fashion.

Cited by 60 publications

References 57 publications

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Organocatálise Enantiosseletiva: Evolução E Aspectos Recentes

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

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