Deracemization of thiol esters of alpha-arylpropionic acids

Marco CLERICUZIO; I DEGANI; S DUGHERA; R. FOCHI

Deracemization of thiol esters of alpha-arylpropionic acids

Marco CLERICUZIO, I DEGANI, S DUGHERA, R. FOCHI

Dipartimento di Scienze e Innovazione Tecnologica

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Racemic thiol esters of α-arylpropionic acids were deracemized by a procedure which featured deprotonation with LDA or KHMDS, transformation into the TMS or TBDMS enol ethers, and enantioselective protonation of the silyl enol ethers using (R)-1,1′-bi-2-naphthol/SnCl₄. Oxidative hydrolysis of the enantiomerically enriched mixtures of thiol esters thus obtained yielded the (S)-enantiomers of ibuprofen and naproxen with ees up to 82%.

Lingua originale	Inglese
pagine (da-a)	119-125
Numero di pagine	7
Rivista	TETRAHEDRON-ASYMMETRY
Volume	14
Stato di pubblicazione	Pubblicato - 2003

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http://hdl.handle.net/11579/18298

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@article{7aa0b46172944fd1a229e2a022366150,

title = "Deracemization of thiol esters of alpha-arylpropionic acids",

abstract = "Racemic thiol esters of α-arylpropionic acids were deracemized by a procedure which featured deprotonation with LDA or KHMDS, transformation into the TMS or TBDMS enol ethers, and enantioselective protonation of the silyl enol ethers using (R)-1,1′-bi-2-naphthol/SnCl4. Oxidative hydrolysis of the enantiomerically enriched mixtures of thiol esters thus obtained yielded the (S)-enantiomers of ibuprofen and naproxen with ees up to 82\%.",

author = "Marco CLERICUZIO and I DEGANI and S DUGHERA and R. FOCHI",

note = "Funding Information: Financial support for the present work was received from the National Research Council of Italy (CNR), and by University of Torino. We kindly acknowledge Professor C. Bicchi (University of Turin, Italy) for the optimization of the chiral stationary phase used in gas-chromatography, and Dr. A. Iuliano (University of Pisa, Italy) for chiral HPLC measurements. ",

year = "2003",

language = "English",

volume = "14",

pages = "119--125",

journal = "TETRAHEDRON-ASYMMETRY",

issn = "0957-4166",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - Deracemization of thiol esters of alpha-arylpropionic acids

AU - CLERICUZIO, Marco

AU - DEGANI, I

AU - DUGHERA, S

AU - FOCHI, R.

N1 - Funding Information: Financial support for the present work was received from the National Research Council of Italy (CNR), and by University of Torino. We kindly acknowledge Professor C. Bicchi (University of Turin, Italy) for the optimization of the chiral stationary phase used in gas-chromatography, and Dr. A. Iuliano (University of Pisa, Italy) for chiral HPLC measurements.

PY - 2003

Y1 - 2003

N2 - Racemic thiol esters of α-arylpropionic acids were deracemized by a procedure which featured deprotonation with LDA or KHMDS, transformation into the TMS or TBDMS enol ethers, and enantioselective protonation of the silyl enol ethers using (R)-1,1′-bi-2-naphthol/SnCl4. Oxidative hydrolysis of the enantiomerically enriched mixtures of thiol esters thus obtained yielded the (S)-enantiomers of ibuprofen and naproxen with ees up to 82%.

AB - Racemic thiol esters of α-arylpropionic acids were deracemized by a procedure which featured deprotonation with LDA or KHMDS, transformation into the TMS or TBDMS enol ethers, and enantioselective protonation of the silyl enol ethers using (R)-1,1′-bi-2-naphthol/SnCl4. Oxidative hydrolysis of the enantiomerically enriched mixtures of thiol esters thus obtained yielded the (S)-enantiomers of ibuprofen and naproxen with ees up to 82%.

UR - https://iris.uniupo.it/handle/11579/18298

M3 - Article

SN - 0957-4166

VL - 14

SP - 119

EP - 125

JO - TETRAHEDRON-ASYMMETRY

JF - TETRAHEDRON-ASYMMETRY

ER -

Deracemization of thiol esters of alpha-arylpropionic acids

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