Chapter 18. Imidazolidinones as Asymmetric Organocatalysts

Cozzi, Pier Giorgio; Gualandi, Andrea; Mengozzi, Luca; Wilson, Claire M.

doi:10.1039/9781782626435-00164

Cited by 4 publications

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“…In this context, an important challenge is represented by the design and synthesis of structurally innovative organocatalysts. Starting from the first employed entities, such as natural proline and derivatives [7,8], MacMillan's imidazolidinones [9], and Jørgensen and Hayashi's diarylprolinol silyl ethers [10,11] (Figure 1a), a huge number of diverse pyrrolidine-based chiral organocatalysts have been proposed. The peculiar structure and substitution pattern of these organocatalysts determine the activation mode of the catalyst, leading to an enantioselective transformation (Figure 1b-e) [12,13].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

2023

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In 1971, chemists from Hoffmann-La Roche and Schering AG independently discovered a new asymmetric intramolecular aldol reaction catalyzed by the natural amino acid proline, a transformation now known as the Hajos–Parrish–Eder–Sauer–Wiechert reaction. These remarkable results remained forgotten until List and Barbas reported in 2000 that L-proline was also able to catalyze intermolecular aldol reactions with non-negligible enantioselectivities. In the same year, MacMillan reported on asymmetric Diels–Alder cycloadditions which were efficiently catalyzed by imidazolidinones deriving from natural amino acids. These two seminal reports marked the birth of modern asymmetric organocatalysis. A further important breakthrough in this field happened in 2005, when Jørgensen and Hayashi independently proposed the use of diarylprolinol silyl ethers for the asymmetric functionalization of aldehydes. During the last 20 years, asymmetric organocatalysis has emerged as a very powerful tool for the facile construction of complex molecular architectures. Along the way, a deeper knowledge of organocatalytic reaction mechanisms has been acquired, allowing for the fine-tuning of the structures of privileged catalysts or proposing completely new molecular entities that are able to efficiently catalyze these transformations. This review highlights the most recent advances in the asymmetric synthesis of organocatalysts deriving from or related to proline, starting from 2008.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

2023

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“…1 d Metal-free acid catalysed dehydrative substitutions of alcohols have also been explored. 4 Acid catalysed synthesis of 3-aryl-benzofuran-2(3 H )-ones was also achieved using the Friedel–Crafts reaction of a 3-hydroxy-benzofuran-2(3 H )-one, a secondary alcohol. 5 a , b However, most of the reported methods utilize either a tailored catalyst, or lack from the substrate diversity.…”

Section: Introductionmentioning

confidence: 99%

A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3H)-ones

et al. 2022

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“…Given the prevalence of this substitution pattern, we reasoned that drug design would potentially benefit from a methodology for the asymmetric construction of chiral 4-imidazolidinones bearing fully substituted tertiary stereocenters. 4-Imidazolidinones have also been used as chiral auxiliaries in the preparation of artificial amino acids and have found applications in popular organic catalysts, but to our knowledge, preparation of these species has been largely restricted to processes involving the use of chiral pool materials or kinetic resolution.…”

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Synthesis of Enantioenriched gem-Disubstituted 4-Imidazolidinones by Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

2021

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A variety of enantioenriched gem-disubstituted 4-imidazolidinones were prepared in up to >99% yield and 95% ee by the Pd-catalyzed decarboxylative asymmetric allylic alkylation of imidazolidinone-derived β-amidoesters. In the process of preparing these substrates, a rapid synthetic route to 4-imidazolidinone derivatives was developed, beginning from 2-thiohydantoin. The orthogonality of the benzoyl imide and tert-butyl carbamate groups used to protect these nitrogen-rich products was demonstrated, enabling potential applications in drug design.

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Chapter 18. Imidazolidinones as Asymmetric Organocatalysts

Cited by 4 publications

References 0 publications

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3H)-ones

Synthesis of Enantioenriched gem-Disubstituted 4-Imidazolidinones by Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

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