Kinetic resolution of racemic α-hydroxy ketones by lipase-catalyzed irreversible transesterification

Adam, Waldemar; Diaz, M. T.; Fell, Rainer T.; Saha‐Möller, Chantu R.

doi:10.1016/0957-4166(96)00272-8

Cited by 53 publications

(15 citation statements)

References 18 publications

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“…Asymmetric α‐aminoxylation of ketone with nitrosobenzene using ( S )‐proline as catalyst followed by the treatment with CuSO 4 gave ( R )‐ 7 in >99% ee ,25 but the synthesis requires 20 mol% catalyst and a stoichiometric amount of the oxidation regent. Enzymatic preparations26 of chiral cyclic α‐hydroxy ketones have been thus far not very enantioselective: kinetic resolution via enantioselective acetylation to give ( S )‐ 10 showed an E of 16–35;27 and reductive kinetic resolution afforded ( R )‐ 6 with an E of 10 3. Thus, our method for the preparation of ( R )‐ 6 – 10 has significant advantages over other reported methods.…”

Section: Methodsmentioning

confidence: 92%

Mechanistic Insight into the CO₂ Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

Zhu¹,

An²

2013

Chemistry An Asian Journal

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CO2 capture has attracted increasing attention owing to its contribution to global warming and climate change as a greenhouse gas. As an alternative strategy to transition-metal-based chemistry and catalysis, frustrated Lewis pairs have been developed to sequester CO2 efficiently under mild conditions. However, the mechanism of CO2 sequestration with amidophosphoranes remains unclear. Herein, we present a thorough density functional theory study on a series of amidophosphoranes. Our results reveal that the interplay of the ring strain and the trans influence determines the reactivities, thus opening a new avenue to the design of frustrated Lewis pairs for CO2 capture.

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Section: Methodsmentioning

confidence: 92%

Mechanistic Insight into the CO₂ Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

Zhu¹,

An²

2013

Chemistry An Asian Journal

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“…[7a] [9] , the values of the optical rotations are given in ref. [10] . After stirring over molecular sieves (4 Å ) for the time stated in Table 1, satd.…”

Section: Methodsmentioning

confidence: 95%

Optically Active Epoxy Diols by Titanium-Catalyzed Oxidation of Enantiomerically Enriched Hydroperoxy and Hydroxy Homoallylic Alcohols

1998

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The Ti‐catalyzed epoxidation of optically active (S,S)‐hydroperoxy homoallylic alcohols 2 affords the epoxy diol (S,R,S)‐4 in high diastereoselectivity (d.r. up to 95:5), while the optically active hydroxy homoallylic alcohols (R,R)‐3 are epoxidized by the β‐hydroperoxy alcohol 5 under titanium catalysis to the corresponding epoxy (R,S,R)‐diol 4 in a diastereomeric ratio up to > 99:1. This high diastereoselectivity is rationalized in terms of a rigid template for the oxygen transfer, in which the hydroperoxy alcohol 2 or 5 is ligated tridentately and the diol 3 bound bidentately to the titanium metal. Through these oxidative routes, both enantiomeric epoxy diols 4 are conveniently accessible.

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“…In that case, transferability of the reaction conditions to a broad set of similar kinetic resolutions almost irrespective of the enzyme catalyst can be expected, including, for instance, conversion of PAC 1 a and HPP 1 b with lipases Amano PS and Amano AK as described by Adam et al …”

Section: Methodsmentioning

confidence: 97%

Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application

Petrenz-Beck

Kühn²,

Zuhse³

et al. 2019

ChemistrySelect

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α‐Hydroxy ketones are important intermediates in various drugs and fine chemicals. Stereoselective synthesis of both symmetric and asymmetric compounds is demonstrated involving benzoin, 2–2’‐furoin, phenylacetyl carbinol (PAC) and 2‐hydroxy‐1‐phenylpropan‐1‐one (HPP) as representatives. Dynamic kinetic resolution of the racemic preparations was achieved in one‐pot combining transesterification catalyzed by immobilized lipases from Pseudomonas stutzeri and Pseudozyma antarctica, respectively, and racemization mediated by the heterogeneous chemo‐catalyst Zr‐TUD‐1 in water‐free organic solvent. (S)‐benzoin, (S)‐2,2’‐furoin, (S)‐PAC and (R)‐HPP were obtained with both high efficiency and high enantiomeric excess. Within 90 minutes, 2,45 g (S)‐PAC butyrate (ee 88%) yielded from a 130 mL batch reaction demonstrating both technical feasibility and relevance for application.

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Kinetic resolution of racemic α-hydroxy ketones by lipase-catalyzed irreversible transesterification

Cited by 53 publications

References 18 publications

Mechanistic Insight into the CO₂ Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

Mechanistic Insight into the CO₂ Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

Optically Active Epoxy Diols by Titanium-Catalyzed Oxidation of Enantiomerically Enriched Hydroperoxy and Hydroxy Homoallylic Alcohols

Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application

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Kinetic resolution of racemic α-hydroxy ketones by lipase-catalyzed irreversible transesterification

Cited by 53 publications

References 18 publications

Mechanistic Insight into the CO2 Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

Mechanistic Insight into the CO2 Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

Optically Active Epoxy Diols by Titanium-Catalyzed Oxidation of Enantiomerically Enriched Hydroperoxy and Hydroxy Homoallylic Alcohols

Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application

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Product

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Mechanistic Insight into the CO₂ Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

Mechanistic Insight into the CO₂ Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs