The synthesis of optically active building blocks carrying a monofluoromethyl group

Kitazume, Tomoya; Asai, Masatomo; Lin, J. T.; Yamazaki, Takashi

doi:10.1016/s0022-1139(00)81995-8

Cited by 19 publications

(2 citation statements)

References 7 publications

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“…Previous results obtained in the acylation of rac - 4 catalyzed by PLE in the presence of MPEG (termed in the following PLE/MPEG- catalyzed acylation) seemed to indicate a particular affinity of PLE in organic solvents toward homobenzylic alcohols . Second, the aforementioned alcohols in enantiomerically enriched form are of synthetic value. − Third, their lipase catalyzed kinetic acylation has to the best of our knowledge not been described. Included into this study were the racemic alcohols rac - 5 and rac - 8 − 10 .…”

Section: Resultsmentioning

confidence: 95%

Activation of Pig Liver Esterase in Organic Media with Organic Polymers. Application to the Enantioselective Acylation of Racemic Functionalized Secondary Alcohols

2001

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Pig liver esterase (PLE) shows practically no activity in acylation of alcohols with vinylic esters in organic solvents. However, addition of methoxypoly(ethylene glycol) (MPEG), bovine serum albumin (BSA), TentaGelAmino resin (TGA), or aminomethyl polystyrene (AMPS) confers activity to PLE in acylation of alcohols with vinyl propionate in organic solvents of low water content. Polymer-activated PLE showed high enantioselectivities (E > 100) in the acylation of racemic 1-alkoxy-, 1-ethylsulfanyl-, and 1-fluoro-3-aryl-2-propanols as well as racemic 1-phenoxy-2-propanol and racemic 1-methoxy-2-phenoxy-2-propanol. The synthetic utility of polymer-activated PLE has been demonstrated by the gram-scale resolution of 1-methoxy-3-phenyl-2-propanol, 1-ethylsulfanyl-3-phenyl-2-propanol, 1-methoxy-3-p-methoxyphenyl-2-propanol, 1-fluoro-3-phenyl-2-propanol, and 1-methoxy-3-phenoxy-2-propanol. In PLE-catalyzed acylation of alcohols with vinyl propionate, acetaldehyde and propionic acids, both being detrimental to the enzyme, are formed as byproducts. In addition, the water content of the system, which is critical for the activity of pig liver esterase, is lowered because of a competing enzymatic hydrolysis of the acyl donor. The polymers TGA, BSA, and AMPS not only scavenge the aldehyde and the acid through imine formation and neutralization, respectively, but replenish at least in part also the water consumed in the competing hydrolysis of the acyl donor. A recovery of PLE together with the polymer was achieved without major loss of activity through their immobilization on a water-saturated polyaramide membrane, which occurs spontaneously in organic solvents.

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Section: Resultsmentioning

confidence: 95%

Activation of Pig Liver Esterase in Organic Media with Organic Polymers. Application to the Enantioselective Acylation of Racemic Functionalized Secondary Alcohols

2001

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“…When substituted 2-acetoxy-1-fluoroalkanes were subjected to hydrolysis with CCL the corresponding fluorohydrins were formed with enantiomeric excesses between 16 and 81% [154]. The reaction was much less selective, when a phenylthio substituent was placed in the molecule [49].…”

Section: Resolution Of Racemic Vicinal Fluorohydrins Using Enzyme-catmentioning

confidence: 99%

Regio- and stereoselective synthesis of vicinal fluorohydrins

Haufe

2004

Journal of Fluorine Chemistry

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New efficient chiral derivatizing agent, ?-cyano-?-fluoro(2-naphthyl)acetic acid (2-CFNA). Application to the EE determination of (?)-3-acetoxy-2-fluoro-2-(hexadecyloxymethyl)propan-1-ol

et al. 2000

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The synthesis of optically active building blocks carrying a monofluoromethyl group

Cited by 19 publications

References 7 publications

Activation of Pig Liver Esterase in Organic Media with Organic Polymers. Application to the Enantioselective Acylation of Racemic Functionalized Secondary Alcohols

Activation of Pig Liver Esterase in Organic Media with Organic Polymers. Application to the Enantioselective Acylation of Racemic Functionalized Secondary Alcohols

Regio- and stereoselective synthesis of vicinal fluorohydrins

New efficient chiral derivatizing agent, ?-cyano-?-fluoro(2-naphthyl)acetic acid (2-CFNA). Application to the EE determination of (?)-3-acetoxy-2-fluoro-2-(hexadecyloxymethyl)propan-1-ol

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