Stereoselective Synthesis of anti‐β‐Hydroxy‐α‐amino Acids Through Dynamic Kinetic Resolution.

Makino, Kazuishi; Goto, Takayuki; Hiroki, Yasuhiro; Hamada, Y.

doi:10.1002/chin.200422197

Cited by 6 publications

(7 citation statements)

References 1 publication

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“…In addition, b-hydroxy-a-amino acids are used as chiral building blocks in preparing precursors to important molecules [132][133][134][135][136][137]. Currently, various synthetic methods have been developed to prepare b-hydroxy-a- amino acids stereoselectively, which include asymmetric aldol reaction [138][139][140][141][142][143][144][145][146][147][148][149][150][151][152][153][154][155][156], alkylation [153][154][155][156], electrophilic amination and allylic amination [157,158], conjugate addition [159], cyanation [160], enantioselective hydrogenation [161], selective hydrolysis [135], rearrangement [162][163][164][165], regioselective aziridine ring opening [135,[166][167][168], dynamic kinetic resolution (DKR) [169][170]…”

Section: Noncoded Amino Acids By Chemical Modification Of Coded Aminomentioning

confidence: 99%

“…This methodology was pioneered by Noyori et al by utilizing the Ru-(R)-2,2 0 -bis(diphenylphosphanyl)-1,1 0 -binaphthyl (BINAP) under 100 atm of hydrogen to obtain syn-selective b-hydroxy-aamino acids from a-amino-b-keto esters [171]. In contrast, Hamada et al used a Ru-(S)-BINAP catalyst to prepare anti-selective b-hydroxy-a-amino acids [169]. In both cases, the yield of product was good, with high diastereo-and enantioselectivity.…”

Section: Noncoded Amino Acids By Chemical Modification Of Coded Aminomentioning

confidence: 99%

See 1 more Smart Citation

Methods for the Chemical Synthesis of Noncoded α‐Amino Acids found in Natural Product Peptides

Habay

Park

Kennedy

et al. 2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Section: Noncoded Amino Acids By Chemical Modification Of Coded Aminomentioning

confidence: 99%

Section: Noncoded Amino Acids By Chemical Modification Of Coded Aminomentioning

confidence: 99%

Methods for the Chemical Synthesis of Noncoded α‐Amino Acids found in Natural Product Peptides

Habay

Park

Kennedy

et al. 2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…The most common technique for obtaining enantiopure compounds on a commercial scale is classical resolution by crystallization, but it is not always applicable. [4] Other techniques such as liquid membrane, [5] chromatographic techniques, [6] and kinetic resolution, [7] accelerate the research on chiral compounds, but they show some defects in large-scale production for most racemic compounds. Chiral extraction accompanied by the reversible complexation between enantioselective extractants and enantiomers can be considered as an alternative to the conventional separation techniques for the resolution of chiral compounds.…”

Section: Introductionmentioning

confidence: 99%

Kinetic Study for Biphasic Recognition Chiral Extraction of Naproxen Enantiomers with HydrophobicL-iso-butyl Tartrate and Hydrophilic Hydroxypropyl-β-Cyclodextrin

Tang

Liu

2012

Solvent Extraction and Ion Exchange

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The kinetics of biphasic recognition chiral extraction of naproxen (HA) enantiomers was investigated to determine the extraction mechanism, with hydrophobic L-iso-butyl tartrate (L-IBTA) in the organic phase and hydrophilic hydroxypropyl-β-cyclodextrin (HP-β-CD) in the aqueous phase. The two-phase homogeneous reaction model was selected over the interfacial reaction model, because there is a clear physical solubility of naproxen enantiomers in both the aqueous phase and the organic phase. The reactions between the HA enantiomers and L-iso-butyl tartrate in a stirred cell fall in Regime 3; the extraction is accompanied by two fast chemical reactions in the diffusion film. The reactions have been found to be first order with respect to HA enantiomers and second order with respect to L-IBTA. The forward rate constants for S-HA and R-HA are 1.26 × 10 −4 mol −2 m 6 s −1 and 2.52 × 10 −4 mol −2 m 6 s −1 , respectively. With the increase of HP-β-CD concentration in the aqueous phase, high enantioselectivity was obtained, but the extraction rates decreased. These data will be useful in the design of extraction processes.

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“…Enantioselective separation methods employed to produce optically pure compounds include diastereomeric crystallization [7,8], kinetic resolution [9][10][11][12] and chiral chromatography [13][14][15]. Each of these methods may have certain advantages (efficiency, practicality, economy, etc.)…”

Section: Introductionmentioning

confidence: 99%

Kinetic study on reactive extraction for chiral separation of phenylsuccinic acid enantiomers

et al. 2010

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The kinetics of the extraction of phenylsuccinic acid (PSA) enantiomers by hydroxypropyl--cyclodextrin (HP--CD) in a modified Lewis cell was studied, in which HP--CD dissolved in 0.1 mol L 1 NaH 2 PO 4 /H 3 PO 4 buffer solution (pH = 2.5) was selected as the chiral extractant. PSA enantiomers were extracted from organic phase to aqueous phase in the extraction module. The theory of extraction accompanied by a chemical reaction has been used to obtain the intrinsic kinetics of this extraction module. The different parameters affecting the extraction rate such as agitation speed, interfacial area, initial concentration of PSA enantiomers in organic phase as well as HP--CD concentration in aqueous phase were separately studied. The experimental results demonstrate that the extraction reactions are fast. The reactions were found to be first order with respect to PSA and second order with respect to HP--CD with forward rate constants of 3.4 × 10 2 m 6 mol 2 s 1 for R-PSA and 9.96 × 10 3 m 6 mol 2 s 1 for S-PSA. These data will be useful in the design of extraction processes.

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Stereoselective Synthesis of anti‐β‐Hydroxy‐α‐amino Acids Through Dynamic Kinetic Resolution.

Cited by 6 publications

References 1 publication

Methods for the Chemical Synthesis of Noncoded α‐Amino Acids found in Natural Product Peptides

Methods for the Chemical Synthesis of Noncoded α‐Amino Acids found in Natural Product Peptides

Kinetic Study for Biphasic Recognition Chiral Extraction of Naproxen Enantiomers with HydrophobicL-iso-butyl Tartrate and Hydrophilic Hydroxypropyl-β-Cyclodextrin

Kinetic study on reactive extraction for chiral separation of phenylsuccinic acid enantiomers

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