Resolution of chiral alcohols with mandelic acid

Whitesell, James K.; Reynolds, Dan W.

doi:10.1021/jo00168a035

Cited by 122 publications

(56 citation statements)

References 2 publications

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“…37,38 Pig liver acetone powder (PLAP) catalyzed hydrolysis of alkyl α-acetoxy-α-phenylacetates produces alkyl (S)-α-phenyl-α-hydroxyacetates in 23-80% enantiomeric purities, 39 and in 22-40% isolated yields. 33 Enantioselectivity is dependent on the …”

Section: Methodsmentioning

confidence: 99%

Applications of liver acetone powders in enantioselective synthesis

Basavaiah¹

2001

Arkivoc

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Applications of liver acetone powders (crude enzymes) as possible substitutes for purified enzyme preparations, hydrolases, in enantioselective organic transformations have been systematically investigated. (1R, 2R)-2-(4-Alkylphenoxy)cyclohexan-1-ols, (1R, 2R)-& (1S, 2S)-2-nitroxycyclohexan-1-ols, (1R, 2S)-2-arylcyclohexan-1-ols, (3R, 4R)-6-methyl-3-phenylhept-1-en-4-ol, and (R)-1-(naphth-1-yl)ethanol have been synthesized in enantiomerically pure form via the enantioselective hydrolysis of the corresponding racemic acetates mediated by liver acetone powders.

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Section: Methodsmentioning

confidence: 99%

Applications of liver acetone powders in enantioselective synthesis

Basavaiah¹

2001

Arkivoc

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“…They are also valuable chiral synthons that have been widely employed for the resolution of racemic compounds, like alcohols and amines (Whitesell and Reynolds, 1983;Hansen et al, 2009;Schramm and Christoffers, 2009). Thus, many methods have been reported for the separation of optically pure (S)-or (R)-mandelic acid (Takahashi et al, 1995;Guo et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Separation of mandelic acid and its derivatives with new immobilized cellulose chiral stationary phase

Zhou

Liu

et al. 2013

J. Zhejiang Univ. Sci. B

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Abstract:A new liquid chromatographic method has been developed for the chiral separation of the enantiomers of mandelic acid and their derivatives 2-chloromandelic acid, 4-hydroxymandelic acid, 4-methoxymandelic acid, and 3,4,5-trismethoxymandelic acid. The enantiomers were separated by a CHIRALPAK ® IC (250 mm×4.6 mm, 5 μm). Mandelic acid, 4-methoxymandelic acid, and 3,4,5-trismethoxymandelic acid were baseline resolved (resolution factor (R S )=2.21, R S =2.14, and R S =3.70, respectively). In contrast, the enantioselectivities between CHIRALPAK ® IC and 2-chloromandelic acid and 4-hydroxymandelic acid investigated were low. By comparing the chromatographs of mandelic acid enantiomers and mandelic acid spiked with (R)-mandelic acid, it was determined that the first effluent was (R)-mandelic acid.

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“…4,5 Non-aqueous systems are particularly useful for chiral synthesis or resolution. 6,7 The use of enzymes in both macro-and micro-aqueous systems has been investigated over the years. Although enzymes exhibit considerable activity in non-aqueous media, the activity is low compared with that in water.…”

Section: Introductionmentioning

confidence: 99%

“…20,21 Mandelic acid enantiomers are important chiral analogs used for the resolution of racemic alcohols and amines. 6,7,22 R-(−)-mandelic acid is a useful raw material for the production of semi-synthetic penicillins and cephalosporins and also for the synthesis of various other pharmaceuticals. 6,23,24 Further, they are also used in the prevention and treatment of honeybee diseases, for human and animal toxoplasmosis and in the synthesis of agrochemicals.…”

Section: Introductionmentioning

confidence: 99%

“…6,7,22 R-(−)-mandelic acid is a useful raw material for the production of semi-synthetic penicillins and cephalosporins and also for the synthesis of various other pharmaceuticals. 6,23,24 Further, they are also used in the prevention and treatment of honeybee diseases, for human and animal toxoplasmosis and in the synthesis of agrochemicals. R-(−)-mandelic acid has been prepared by the microbiological hydrolysis of mandelic acid derivatives, 25,26 asymmetric reduction of benzoylformic acid with microorganisms, 27 microbial oxidation of 1-phenyl-1,2-ethanediol, 28 microbial oxidation of racemic mandelic acid 29 and enzymatic asymmetric synthesis from n-keto aldehyde.…”

Section: Introductionmentioning

confidence: 99%

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Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of RS‐( ± )‐methyl mandelate

Yadav

Sajgure

Dhoot

2008

J of Chemical Tech & Biotech

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BACKGROUND: Mandelic acid enantiomers are important chiral analogs used for the resolution of racemic alcohols and amines. R-(−)-mandelic acid is a precursor for the production of semi-synthetic penicillins and cephalosporins and also for the synthesis of various pharmaceuticals. Production of optically pure mandelic acid enantiomers is commercially significant. This work deals with the resolution of RS-(±)-methyl mandelate to produce optically pure R-(−)-mandelic acid in non-aqueous media via lipase-catalyzed hydrolysis under microwave irradiation.

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Resolution of chiral alcohols with mandelic acid

Cited by 122 publications

References 2 publications

Applications of liver acetone powders in enantioselective synthesis

Applications of liver acetone powders in enantioselective synthesis

Separation of mandelic acid and its derivatives with new immobilized cellulose chiral stationary phase

Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of RS‐( ± )‐methyl mandelate

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