Facile synthesis of cyclic α-perfluoroalkyl-α-aminophosphonates

Odinets, Irina L.; Аrtyushin, О. I.; Shevchenko, Nikolay E.; Nenajdenko, V. G.; Röschenthaler, Gerd‐Volker

doi:10.1016/j.jfluchem.2009.05.002

Cited by 24 publications

(9 citation statements)

References 41 publications

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“…Within this approach, the reaction of 1-pyrroline derivatives with hydrophosphoryl compounds (Pudovik reaction) is used the most widely (Scheme 1). [21][22][23][24][25] Both 2-aryland 2-alkyl-substituted 1-pyrroline derivatives react smoothly to give appropriate 2-phosphorylpyrrolidines in good to high yields. In general, no catalyst was employed (Scheme 1, A, 21 B, 22 and D 24 ) however in some cases (Scheme 1, B 22 and E 25 ) Lewis acids were used.…”

Section: Syntheses Via Pudovik Reactionmentioning

confidence: 99%

“…For example, the addition of diethyl phosphite to 2-perfluoralkyl-1-pyrrolines does not proceed in the absence of a catalyst. 23 Moreover, even in the presence of a Lewis acid the reaction requires a prolonged time in comparison with a similar reaction in the non-fluorinated series (Scheme 1, C). Nonetheless, the yields of fluorinated compounds were higher (90-94%) than those of their non-fluorinated analogues.…”

Section: Syntheses Via Pudovik Reactionmentioning

confidence: 99%

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Synthesis of Phosphaproline Derivatives: A Short Overview

et al. 2019

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Pyrrolidine-based phosphonates, analogues of the natural amino acid proline, possess a diverse set of biological activity. The goal of this short review is to summarize the major developments in the synthesis of phosphaproline derivatives reported since 2004 with special emphasis on the mechanisms and limitations of the methods presented.1 Introduction2 Phosphorylation of Pyrrolidine Derivatives2.1 Syntheses via Pudovik Reaction2.2 Syntheses via Arbuzov Reaction2.3 Decarboxylative Phosphorylation of Proline2.4 Direct C–H Bond Phosphorylation2.5 Other Reactions2.6 Overview of Phosphorylation Methods3 Synthesis of 2-Phosphorylpyrrolidines from Acyclic Precursors3.1 Cyclization of 4-Substituted Butylamine Derivatives3.2 [3+2]-Dipolar Cycloaddition of α-Iminophosphonates3.3 Cyclization of Aminoalkynes and 4-Aminocarbonyl Compounds4 Conclusions

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Section: Syntheses Via Pudovik Reactionmentioning

confidence: 99%

Section: Syntheses Via Pudovik Reactionmentioning

confidence: 99%

Synthesis of Phosphaproline Derivatives: A Short Overview

et al. 2019

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“…OEt 2 ) as the catalyst, 2-(trifluoromethyl)-2-ethylphosphonate piperidine ( 14 ) was obtained (92%) and easily transformed to the corresponding α-trifluoromethyl substituted cyclic α-aminophosphonic acid 15 by treatment with trimethylbromosilane in CHCl 3 followed by the addition of aqueous MeOH. It is worth pointing out that to avoid the formation of the ammonium salt, due to the liberation of HBr during the hydrolysis of the ester, the addition of propylene oxide was necessary and the free amino acid 15 was isolated (Scheme 9) [16]. …”

Section: From Cyclic Substratesmentioning

confidence: 99%

Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives

Rioton¹,

Pardo²,

Cossy³

2017

Molecules

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A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives by reduction, and from 5-membered rings e.g., prolinol derivatives by ring expansion, from linear amines by cyclization or from dienes/dienophiles by [4 + 2]-cycloaddition.

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“…Phosphoprolines, as well as pyrrolidines themselves, are available via diverse methods. [28][29][30][31][32][33] In contrast, the number of approaches to N-phosphorylpyrrolidines is quite limited. The most common and obvious entry to N-phosphorylpyrrolidines is vis phosphorylation of N-unprotected pyrrolidines with P(III) and P(V) derivatives.…”

Section: Introductionmentioning

confidence: 99%

N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

et al. 2020

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Organophosphorus pyrrolidine derivatives possessing P–N bonds are a promising yet underexplored class of compounds. In this short review we overview the general approaches to these compounds described so far, with a special emphasis on their asymmetric synthesis.1 Introduction2 Synthesis of Pyrrolidine-Based P(III) Derivatives3 Synthesis of Pyrrolidine-Based P(V) Derivatives3.1 Phosphorylation of Pyrrolidines with P(V) Acid Chlorides3.2 Phosphorylation of Pyrrolidines with P(V) Acid Esters3.3 Syntheses via the Atherton–Todd Reaction3.4 Oxidation of Pyrrolidine-Based P(III) Derivatives4 Syntheses of N-Phosphorylpyrrolidines from Acyclic Precursors5 Conclusions

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Facile synthesis of cyclic α-perfluoroalkyl-α-aminophosphonates

Cited by 24 publications

References 41 publications

Synthesis of Phosphaproline Derivatives: A Short Overview

Synthesis of Phosphaproline Derivatives: A Short Overview

Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives

N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

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