Resolution of enantiomers of [α-hydroxy-(o-chlorophenyl)methyl]phosphinic acid via diastereomeric salt formation with enantiopure 1-phenylethylamines

Kaboudin, Babak; Alaie, Saied; Yokomatsu, Tsutomu

doi:10.1016/j.tetasy.2011.10.019

Cited by 12 publications

(5 citation statements)

References 39 publications

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“…Salt (R,S)-7a was found to precipitate from a mixture of (±)-5 and (S)-1-phenylethylamine in MeOH-ACN at room temperature. 22,23 The 31 P NMR spectrum of the crystallized salt 7a exhibited a singlet at δ = 18.92 ppm. The selection of the (R)-enantiomer of rac-5 with (S)-1-phenylethylamine was confirmed by X-ray crystallography 34 (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Determination of the absolute configuration of phosphinic analogues of glutamate

et al. 2015

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A series of phosphinic glutamate derivatives (e.g.LSP1-2111) have been proven to be potent agonists of metabotropic glutamate (mGlu) receptors and shown promising in vivo activity. However, so far all were synthesized and tested as a mixture of two diastereomers whose absolute and relative configurations are not known. In this study, the stereomers were separated on a Crownpack CR(+) column and their absolute configuration was assessed by means of a diastereoselective synthesis. Both separated L-stereomers activated the mGlu4 receptor with EC50's of 0.72 and 4.4 μM for (1S,1'S)-and (1S,1'R)-LSP1-2111, respectively.

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Section: Resultsmentioning

confidence: 99%

“…22,23 The 31 P NMR spectrum of the crystallized salt 7a exhibited a singlet at δ = 18.92 ppm. The selection of the (R)-enantiomer of rac-5 with (S)-1-phenylethylamine was confirmed by X-ray crystallography 34 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Determination of the absolute configuration of phosphinic analogues of glutamate

et al. 2015

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“…Investigation of the resolution of racemic α-hydroxy-( o -chlorophenyl)methyl]phosphinic acid with ( R )-α-PEA via diastereomeric salt formation revealed that the ( R,R )-salt precipitation from 2-propanol was an efficient resolving method for obtaining a single enantiomer of phosphinic acid. Resolving rac -phosphinic acid with ( S )-α-PEA in EtOH by the same procedure gave access to ( S )-acid in 32% yield ( Scheme 11 ) [ 20 ].…”

Section: Application Of Enantiomeric α-Pea In Chiral Resolutionmentioning

confidence: 99%

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Wosińska-Hrydczuk

Skarżewski

2020

Molecules

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New developments in the synthesis, resolution, and synthetic applications of chiral 1-phenylethylamine (α-PEA) reported in the last decade have been reviewed. In particular, improvements in the synthesis of α-PEA and its derivatives and chiral resolution, as well as their applications in the resolution of other compounds, were discussed. α-PEA was used as a chiral auxiliary in the diastereoselective synthesis of medicinal substances and natural products. Chiral ligands with α-PEA moieties were applied in asymmetric reactions, and effective modular chiral organocatalysts were constructed with α-PEA fragments and used in important synthetic reactions.

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“…There is only one literature note discussing the application of d-Bz-L-TA as a chiral resolving agent for the separation of racemic aminophosphonates . As part of our efforts to develop facile and practical methods for the separation of racemic phosphonic and phosphinic acid derivatives, − we have recently developed a novel method for the preparation of ( R )- and ( S )-pyrrolidine-2-phosphonic acids through resolution of (±)-diethyl pyrrolidine-2-phosphonate by the formation of diastereomeric amides with d-Bz-L-TA . In our continuous research program directed to the preparation of optically active α-substituted phosphonates, now, we have focused on the method applicable to the resolution of α-hydroxyphosphonates.…”

Section: Introductionmentioning

confidence: 99%

Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)₃-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride

et al. 2019

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A practical and efficient method has been developed for the preparation of optically active α-hydroxyphosphonates through resolution of the racemates. Treatment of racemic diethyl 1-hydroxy-1-phenylmethylphosphonate (1) with (+)-dibenzoyl-L-tartaric anhydride gave two diastereomeric esters 2 and 3 in the presence of bismuth triflate (15 mol %) in an 86:14 ratio. The two diastereomeric esters were separated by simple column chromatography, and the structure for the major diastereomer was determined by X-ray crystallographic analysis. Simple hydrolysis of the isolated major diastereomer in the usual manner afforded (R)-O,O-diethyl-1-[hydroxyl(phenyl)methyl] phosphonate 1. The advantages of the present method are that the operation is simple and easy to handle, along with rapid and good yield preparations of both enantiomers of the racemic α-phosphonates 1. Diastereoselective reactions of various racemic α-hydroxyphosphonates with d-Bz-L-TA in the presence of Bi(OTf)3 are also described.

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Resolution of enantiomers of [α-hydroxy-(o-chlorophenyl)methyl]phosphinic acid via diastereomeric salt formation with enantiopure 1-phenylethylamines

Cited by 12 publications

References 39 publications

Determination of the absolute configuration of phosphinic analogues of glutamate

Determination of the absolute configuration of phosphinic analogues of glutamate

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)₃-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride

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Resolution of enantiomers of [α-hydroxy-(o-chlorophenyl)methyl]phosphinic acid via diastereomeric salt formation with enantiopure 1-phenylethylamines

Cited by 12 publications

References 39 publications

Determination of the absolute configuration of phosphinic analogues of glutamate

Determination of the absolute configuration of phosphinic analogues of glutamate

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride

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Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)₃-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride