N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

Smolobochkin, Аndrey V.; Газизов, А. С.; Турманов, Рахымжан А.; Abdullaeva, Dinara S.; Бурилов, А. Р.; Пудовик, М. А.

doi:10.1055/s-0039-1690889

Cited by 4 publications

(2 citation statements)

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“…In spite of this, the number of approaches to (pyrrolidin‐1‐yl)phosphoramidates is quite limited, as demonstrated in our recent review . The formation of a P−N bond is usually achieved via phosphorylation of N ‐unsubstituted pyrrolidines by P(V) acid chlorides, which is a general method of synthesis of phosphoramidates.…”

Section: Methodsmentioning

confidence: 99%

2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

et al. 2020

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A first successful synthesis of 2-(het)aryl-N-phosphorylpyrrolidines is reported starting from readily available N-(4,4-diethoxybutyl)amides of P(V) acids. A range of phenols and hydroxyl-substituted O-heterocycles may be employed into the reaction furnishing N-phosphorylated 2-(het)arylpyrrolidines with up to 90 % yield. The developed method permits a presence of sensitive to phosphorylation hydroxy groups and provides the easy and regioselective entry to target compounds. Pyrrolidine core is widespread in natural products [1,2] and synthetic drugs. [3] Phosphorus-containing pyrrolidine derivatives are of a special interest due to their various biological [4-8] and catalytic [9,10] properties. Among them, (pyrrolidin-1-yl) phosphoramidates are proposed for hepatitis C, [11] malaria and tuberculosis [12] treatment, possess anti-HIV [13-16] and antitumor [17,18] activity. Additionally, they employed as chiral ligands in various asymmetric reactions. Examples are metal-catalyzed stereoselective reduction of ketones, [19,20] ketimines [21] and alkenes, [22-24] various cycloadditions, [25-29] addition of boronic acids [30] and organotrifluoroborates [31] to alkenes, asymmetric ruthenium-catalyzed metallo-ene reaction [32] and Suzuki-Miyaura coupling. [33]

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Section: Methodsmentioning

confidence: 99%

2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

et al. 2020

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“…Some reviews surveyed an aspect of the synthetic protocols accord The huge interest in this structural motif has led to great efforts in developing novel and efficient synthetic strategies for the asymmetric construction of substituted chiral pyrrolidines. Some reviews surveyed an aspect of the synthetic protocols according to a peculiar focus, usually related to a specific chemical transformation: asymmetric syntheses of pyrrolidines exploiting organocatalysis [14], asymmetric [3 + 2]-cycloadditions involving azomethine ylides [15], catalytic asymmetric 1,3-dipolar cycloadditions [16], aryl-sulfinamides in the synthesis of N-heterocycles [17], synthesis of N-phosphorylated pyrrolidines [18], annulation strategies for the construction of multisubstituted pyrrolidines as natural products [19], or palladium-catalyzed alkene aminoarylation reactions [20]. Conversely, in this review, we focus on the advances achieved in the last 15 years (between 2008 and 2022) in the asymmetric synthesis of novel chiral pyrrolidine-based organocata-lysts, including all of the proposed synthetic approaches.…”

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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