A facile asymmetric synthesis of 1-amino-2,2,2-trifluoroethanephosphonic acid

Xiao, Jingbo; Zhang, Xiaomei; Yuan, Chengye

doi:10.1002/1098-1071(2000)11:7<536::aid-hc12>3.0.co;2-y

Cited by 37 publications

(10 citation statements)

References 16 publications

(17 reference statements)

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“…In 2000 Xiao et al . proposed facile asymmetric synthesis of 88 (Scheme 14, path A) [103] . In that approach ( S )‐phenylethylamine was used to form chiral imidoyl chloride 96 with trifluoroacetic acid.…”

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

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Amino Acid Based Antimicrobial Agents – Synthesis and Properties

2021

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Structures of several dozen of known antibacterial, antifungal or antiprotozoal agents are based on the amino acid scaffold. In most of them, the amino acid skeleton is of a crucial importance for their antimicrobial activity, since very often they are structural analogs of amino acid intermediates of different microbial biosynthetic pathways. Particularly, some aminophosphonate or aminoboronate analogs of protein amino acids are effective enzyme inhibitors, as structural mimics of tetrahedral transition state intermediates. Synthesis of amino acid antimicrobials is a particular challenge, especially in terms of the need for enantioselective methods, including the asymmetric synthesis. All these issues are addressed in this review, summing up the current state‐of‐the‐art and presenting perspectives fur further progress.

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Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

“…proposed facile asymmetric synthesis of 88 (Scheme 14 , path A). [103] In that approach ( S )‐phenylethylamine was used to form chiral imidoyl chloride 96 with trifluoroacetic acid. Next imidoyl chloride 96 was reacted with triethyl phosphite to introduce a phosphonic group.…”

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

2021

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“…Yuan and coworkers reported that 1-amino-2,2,2-trifluoroethanephosphonic acid was synthesized from ketimine 71 via a base-catalyzed transamination and subsequent hydrolysis (Scheme 23). 41 In 1994, Soloshonok and coworkers reported that b-fluoroalkylb-amino acids were obtained with up to 36% ee via chiral basecatalyzed isomerization of enamines under solvent-free conditions (Scheme 24). 42 In 2007, Plaquevent and coworkers showed that trifluoromethyl enamines such as 78 were isomerized to the This journal is © The Royal Society of Chemistry 2015 corresponding aldimines in up to 71% ee with a dimeric cinchona alkaloid (DHQ) 2 PHAL (Scheme 25).…”

Section: Transamination Of Fluoroalkyl Ketonesmentioning

confidence: 99%

Progress in asymmetric biomimetic transamination of carbonyl compounds

et al. 2015

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Transamination of α-keto acids with transaminases and pyridoxamine phosphate is an important process to form optically active α-amino acids in biological systems. Various biomimetic transamination systems have been developed for carbonyl compounds including α-keto acid derivatives, fluoroalkyl ketones, and unactivated ketones with chiral vitamin B6 analogues, artificial transaminase mimics, chiral nitrogen sources, and chiral catalysts. This review provides a brief summary of this area.

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“…Finally, treatment of ( R )- 259 with concentrated hydro-chloric acid, followed by the addition of propylene oxide afforded the ( R )-α-aminophosphonic acid 260 in 90% yield (Scheme 68). 155…”

Section: Stereoselective Synthesis Of α-Aminophosphonic Acids and mentioning

confidence: 99%

An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives

2009

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An overview of all methodologies published during the last few years focused to the stereoselective (diastereoselective or enantioselective) synthesis of α-aminophosphonic acids and derivatives is reported. The procedures have been classified according a retrosynthetic strategy and taking into account the formation of each one of the bonds connected to the chiral centre. Keywordsα-Aminophosphonic acids; α-Aminophosphonates; Stereoselective Synthesis; Resolution; Chiral Pool Introducciónα-Aminoalkylphosphonic acids 1 are structurally analogous to α-amino acids 2, obtained by isosteric substitution of planar and less bulky carboxylic acid (CO 2 H) by a tetrahedral phosphonic acid functionality (PO 3 H 2 ). Several aminophosphonic, aminophosphinic and aminophosphonous acids have been isolated from various natural sources either as free amino acids or as constituents of more complex molecules. 1 Many natural and synthetic aminophosphonic acids, their phosphonate esters and short peptides incorporating this unit, exhibit a variety of biological properties. 2 Their diverse applications include enzyme inhibitors 3 such as synthase, 4 HIV protease, 5 rennin, 6 phosphatasa activity, 7 PTPases, 8 and potent antibiotics, 9 as antibacterial agents, 10 antiviral, 11 antifungal, 12 herbicides, 13 antitumor agents. 14 Their role for antibody generation is also well documented. 15 In addition, the incorporation of cyclic amino acids of medium ring size into key positions in peptide chains plays an important role, and constitutes the most prominent pathway to conformationally constrained peptidomimetics, a tool in modern drug discovery. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptIn addition, α-aminophosphonic acids and their monoalkyl esters are also of interest in hydrometallurgy in order to extract metals 17 and in diagnostic medicine as screening agents, once complexed with lanthanides and actinides. 18,19 It is well known that the biological activity of α-aminophosphonic acids and derivatives depends on the absolute configuration of the stereogenic α carbon to phosphorous. 20 For example, (R)-phospholeucine 3 is a more potent inhibitor of leucine aminopeptidase than the S enantiomer, 21 and (S,R)-alafosfalin 4 shows higher antibacterial activity against both Grampositive and Gram-negative microorganisms than the other three diastereoisomers. 22 In view of the different biological and chemical applications of the α-aminophosphonic acids and derivatives, in the last 35 years the development of suitable synthetic methodologies for their preparation in optically pure form has been a topic of great interest in several research groups. In this context, several protocols for efficient asymmetric synthesis of α-aminophosphonic acids and derivatives have emerged in the recent years and several reviews have been published. 23 Now we would like to report herein an update over stereoselective synthesis of α-aminophosphonic acids and derivatives from 1998-2007. The principal synthetic stra...

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A facile asymmetric synthesis of 1-amino-2,2,2-trifluoroethanephosphonic acid

Cited by 37 publications

References 16 publications

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

Progress in asymmetric biomimetic transamination of carbonyl compounds

An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives

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