Aminosäuren, 4. Enantioselektive Synthese <i>N</i>‐substituierter α‐Aminocarbonsäuren aus α‐Hydroxycarbonsäuren

Effenberger, Franz; Burkard, Ulrike; Willfahrt, Joachim

doi:10.1002/jlac.198619860213

Cited by 77 publications

(33 citation statements)

References 37 publications

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“…The two furalaxyl enantiomers were prepared via chiral synthesis methods, and the synthetic procedure was the same as synthesis of benalaxyl enantiomers we have discussed in detail …”

Section: Methodsmentioning

confidence: 99%

Enantioselective Acute Toxicity Effects and Bioaccumulation of Furalaxyl in the Earthworm (Eisenia foetida)

et al. 2014

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The enantioselectivities of individual enantiomers of furalaxyl in acute toxicity and bioaccumulation in the earthworm (Eisenia foetida) were studied. The acute toxicity was tested by filter paper contact test. After 48 h of exposure, the calculated LC 50 values of the R-form, rac-form, and S-form were 2.27, 2.08, and 1.22 μg cm -2 , respectively. After 72 h of exposure, the calculated LC 50 values were 1.90, 1.54, and 1.00 μg cm -2 , respectively. Therefore, the acute toxicity of furalaxyl enantiomers was enantioselective. During the bioaccumulation experiment, the enantiomer fraction of furalaxyl in earthworm tissue was observed to deviate from 0.50 and maintained a range of 0.55-0.60; in other words, the bioaccumulation of furalaxyl was enantioselective in earthworm tissue with a preferential accumulation of S-furalaxyl. The uptake kinetic of furalaxyl enantiomers fitted the first-order kinetics well and the calculated kinetic parameters were consistent with the low accumulation efficiency. Chirality 26:307-312, 2014.

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“…The two furalaxyl enantiomers were prepared via chiral synthesis methods, and the synthetic procedure was the same as synthesis of benalaxyl enantiomers we have discussed in detail …”

Section: Methodsmentioning

confidence: 99%

Enantioselective Acute Toxicity Effects and Bioaccumulation of Furalaxyl in the Earthworm (Eisenia foetida)

et al. 2014

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“…[18][19][20] The synthetic procedure was the same as synthesis of benalaxyl enantiomers we have discussed in detail. [18] Acetonitrile (HPLC grade) was obtained from Fisher Scientific (Fair Lawn, NJ, USA).…”

Section: Chemicals and Soilsmentioning

confidence: 99%

Environmental behavior of benalaxyl and furalaxyl enantiomers in agricultural soils

Fang

Gao

Guo

et al. 2014

Journal of Environmental Science and Health, Part B

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The enantioselective environmental behavior of the chiral fungicides benalaxy and furalaxyl in agricultural soils in China was studied. Although sorption onto soils was non-enantioselective, the leaching of benalaxy and furalaxyl was enantioselective in soil columns. The concentrations of the S-enantiomers of both fungicides in the leachates were higher than the R-enantiomers. This can be attributed to enantioselective degradation of the two fungicides in the soil column. Enantioselective degradation of the two fungicides was verified by soil dissipation experiments, and the R-enantiomers degraded faster than the S-enantiomers in partial soils. The half-life was 27.7-57.8 days for S-benalaxyl, 20.4-53.3 days for R-benalaxyl, 19.3-49.5 days for S-furalaxyl and 11.4-34.7 days for R-furalaxyl. The degradation process of the two fungicide enantiomers followed the first-order kinetics (R 2 > 0.96). Compared to furalaxyl, benalaxyl degraded more slowly and degradation was less enantioselective. These results are attributed to the influence of soil physicochemical properties, soil microorganisms, and environmental factors.

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“…These include methods for direct methylation, 1-5 reductive amination, 6-12 alternative methods [13][14][15][16][17][18] and through the generation of oxazolidinones and their subsequent transformation to the N-methyl (alkyl) product. [19][20][21][22][23] In addition, there are strategies involving the use of immonium ions in Diels-Alder/retro-Diels-Alder sequences, 24 the nucleophilic displacement of triflates, 25 the hydroxyamination of chiral enolates 26 and the Mitsunobu reaction. 27 Some of these methods suffer from limitations in the range of amino acids to which they are applicable, some utilize rather long synthetic sequences and some cause at least partial racemisation of the substrate.…”

Section: Introductionmentioning

confidence: 99%

The Facile Production of N-Methyl Amino Acids via Oxazolidinones

et al. 2000

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Aminosäuren, 4. Enantioselektive Synthese N‐substituierter α‐Aminocarbonsäuren aus α‐Hydroxycarbonsäuren

Abstract: (S)-a-(TrifluormethyIsulfonyloxy)carbonsZureester (S)-

Cited by 77 publications

References 37 publications

Enantioselective Acute Toxicity Effects and Bioaccumulation of Furalaxyl in the Earthworm (Eisenia foetida)

Enantioselective Acute Toxicity Effects and Bioaccumulation of Furalaxyl in the Earthworm (Eisenia foetida)

Environmental behavior of benalaxyl and furalaxyl enantiomers in agricultural soils

The Facile Production of N-Methyl Amino Acids via Oxazolidinones

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