Enhanced Diastereoselectivity in the Asymmetric Ugi Reaction Using a New “Convertible” Isonitrile.

Linderman, Russell J.; Binet, Sophie; Petrich, Samantha R.

doi:10.1021/jo994009z

Cited by 4 publications

(2 citation statements)

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“…Polyoxins are a class of nucleoside antibiotics that have a critical natural function in that they oppose chitin synthase (CS). Generally, Polyoxins were isolated from Saccharomyces cerevisiae and Candida albicans due to their antibacterial properties [77]. Chitin synthases are considered attractive targets for inhibition in fungi and insects.…”

Section: The Discovery Of Antimicrobial Compounds Against Infectious ...mentioning

confidence: 99%

The Discovery of Novel Antimicrobial Agents through the Application of Isocyanide-Based Multicomponent Reactions

Quazi

Rashid²,

Malik

et al. 2023

Antibiotics

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Multicomponent reactions (MCR) have been used to synthesize a wide range of analogs from several classes of heterocyclic compounds, with multifaceted medicinal uses. The synthesis of highly functionalized molecules in a single pot is a unique property of MCR, allowing researchers to quickly assemble libraries of compounds of biological interest and uncover novel leads as possible therapeutic agents. Isocyanide-based multicomponent reactions have proven to be extremely effective at swiftly specifying members of compound libraries, particularly in the discovery of drugs. The understanding of structure–activity correlations that drive the development of new goods and technology requires structural variety in these libraries. In today’s world, antibiotic resistance is a major ongoing problem that poses risks to public health. The implementation of isocyanide-based multicomponent reactions upholds a significant potential in this regard. By utilizing such reactions, new antimicrobial compounds can be discovered and subsequently used to fight against such concerns. This study discusses the recent developments in antimicrobial medication discovery using isocyanide-based multicomponent reactions (IMCRs). Furthermore, the article emphasizes the potential of IMCRs (Isocyanide-based multicomponent based reactions) in the near future.

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Section: The Discovery Of Antimicrobial Compounds Against Infectious ...mentioning

confidence: 99%

The Discovery of Novel Antimicrobial Agents through the Application of Isocyanide-Based Multicomponent Reactions

Quazi

Rashid²,

Malik

et al. 2023

Antibiotics

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“…The first diastereoselective N-arylative Ugi-Smiles (US-4CR) reaction using a chiral aldehyde 74 to afford N-aryl amides 75 was reported by Radhakrishna 30 and his group in 2014 (Scheme 39). The reaction proceeds smoothly under optimized conditions to give N-aryl amides in moderate to good yield and diastereomeric ratios.…”

Section: Chiral Aldehydes As Substratementioning

confidence: 99%

A concise review on the stereoselective synthesis of chiral α-bisamides using stereoselective Ugi-type reaction

Ramakrishna¹,

Pradhan²

2021

Arkivoc

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To ensure a sustainable development, the "twelve principles of green chemistry" have been proposed for the field of synthetic organic chemistry. The stereoselective Ugi reaction is one of the most widely used reactions with high atom economy to prepare chiral α-bisamides and this reaction satisfies many of the green chemistry principles. The recent achievements in this reaction include one pot synthetic methodology, aqueous phase transformations and solvent free transformations even at ambient conditions. This review summarizes the progress recorded in this field over the past 20 years.Retrosynthetic methodology for the synthesis of Chiral α-bisamide

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A Half‐Century of the Ugi Reaction: Classic Variant

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process that involves a carboxylic acid, a carbonyl compound, an amine, and an isocyanide. All reaction components are in a dynamic equilibrium with several intermediates, until an irreversible intramolecular 1,4‐ O → N acyl transfer leads to the formation of an N ‐acylamino acid amide. If chiral components are used in this reaction, a mixture of diastereomers is generally formed with moderate‐to‐low stereoselectivity. The broad scope of substrates that can be used in the Ugi reaction allows for the straightforward synthesis of libraries of structurally related amino acid and peptide derivatives. Therefore, this methodology is often applied to the synthesis of drugs, drug‐like molecules, and natural products. This chapter describes different variations of classic Ugi reactions, including the use of functionalized and cleavable reaction components to illustrate the broad scope of the reaction. In addition, applications in target‐directed synthesis and comparisons to other related multicomponent reactions are presented. Tabular surveys are organized according to the isocyanides used. The literature is discussed from the first disclosure of an Ugi reaction in 1961 through to the end of 2012.

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Enhanced Diastereoselectivity in the Asymmetric Ugi Reaction Using a New “Convertible” Isonitrile.

Cited by 4 publications

References 0 publications

The Discovery of Novel Antimicrobial Agents through the Application of Isocyanide-Based Multicomponent Reactions

The Discovery of Novel Antimicrobial Agents through the Application of Isocyanide-Based Multicomponent Reactions

A concise review on the stereoselective synthesis of chiral α-bisamides using stereoselective Ugi-type reaction

A Half‐Century of the Ugi Reaction: Classic Variant

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