Dynamic kinetic resolution

Gihani, M. T. El; Williams, Jonathan M. J.

doi:10.1016/s1367-5931(99)80003-9

Cited by 118 publications

(27 citation statements)

References 18 publications

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“…This is a combination of two reaction systems: (i) the continuous racemization of the alcohol via hydrogen transfer; and (ii) the enantioselective protection of the alcohol using a [122][123][124][125][126][127]. As was first demonstrated by Williams and colleagues [30], a dynamic kinetic resolution of racemic alcohols by the combination of two catalysts provides a mild and effective means of obtaining enantiomerically pure alcohols in high yields and selectivities (Scheme 20.31).…”

Section: Racemizationsmentioning

confidence: 99%

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Klomp¹,

Hanefeld²,

Peters³

2006

The Handbook of Homogeneous Hydrogenation

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Section: Racemizationsmentioning

confidence: 99%

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Klomp¹,

Hanefeld²,

Peters³

2006

The Handbook of Homogeneous Hydrogenation

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“…5,6,8,9,12,13,14,15,16, and 17 for the initial conditions of (S A )=(S A ) 0 , (S B )=(S B ) 0 , (OH À ) = (OH À ) 0 , (H + ) 0 = K w /(OH À ) 0 , ( Q A ) = (Q B ) = (Q AW ) = (Q A-W ) = (Q BW ) = (Q B-W ) = 0 using a fourth-order Runge-Kutta method. When the whole process is operated in a feed-batch mode, the above model is still valid, except that the initial conditions should be modified by considering the mixing effect of adding fresh (R, S)-thioester and NaOH in the organic and aqueous phases, respectively.…”

Section: Dynamic Kinetic Resolution Of (R S)-suprofen Thioestermentioning

confidence: 98%

“…However, using a racemic starting substrate, a standard kinetic resolution process can only produce a maximum 50% yield of the desired enantiomer. Dynamic kinetic resolution has proved to be a potentially efficient process in which the standard kinetic resolution is coupled to continuous in situ racemization of the remaining substrate [4,5,6,7,8,9,10,11,12]. In principle, all of the substrate can be converted into a single enantiomer product with a 100% theoretical yield using this technique.…”

Section: Introductionmentioning

confidence: 98%

Process modeling of the lipase-catalyzed dynamic kinetic resolution of (R, S)-suprofen 2,2,2-trifluoroethyl thioester in a hollow-fiber membrane

Wang

Cheng

Tsai

2004

Bioprocess Biosyst Eng

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A Candida rugosa lipase immobilized on polypropylene powder was employed as the biocatalyst for the enantioselective hydrolysis of (R, S)-suprofen 2,2,2-trifluorothioester in cyclohexane, in which trioctylamine was added as the catalyst to perform in situ racemization of the remaining (R)-thioester. A hollow-fiber membrane was also integrated with the dynamic kinetic resolution process in order to continuously extract the desired (S)-suprofen into an aqueous solution containing NaOH. A kinetic model for the whole process (operating in batch and feed-batch modes) was developed, in which enzymatic hydrolysis and deactivation, lipase activation, racemization and non-enantioselective hydrolysis of the substrate by trioctylamine, and reactive extraction of (R)- and (S)-suprofen into the aqueous phase in the membrane were considered. Theoretical predictions from the model for the time-course variations of substrate and product concentrations in each phase were compared with experimental data.

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“…For economic and ecological reasons, a lot of effort has been put forth to circumvent these limitations. Novel concepts have been developed, such as dynamic kinetic resolution (DKR) [102][103][104][105][106][107][108] with a 100% theoretical yield. The key step to turn a kinetic resolution process into a dynamic process is the in situ racemization of the substrate enantiomers (Scheme 13).…”

Section: A General Remarksmentioning

confidence: 99%