Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application
Abstract 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. Dy...
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crwiley:10.1002/slct.201900740 2024-06-02T07:58:21+00:00 Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application Petrenz‐Beck, Annika Kühn, Jasmin Zuhse, Ralf Ansorge‐Schumacher, Marion B. 2019 http://dx.doi.org/10.1002/slct.201900740 https://onlinelibrary.wiley.com/doi/pdf/10.1002/slct.201900740 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/slct.201900740 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor ChemistrySelect volume 4, issue 21, page 6469-6472 ISSN 2365-6549 2365-6549 journal-article 2019 crwiley https://doi.org/10.1002/slct.201900740 2024-05-03T11:33:45Z Abstract 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. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library ChemistrySelect 4 21 6469 6472 |
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English |
description |
Abstract 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. |
format |
Article in Journal/Newspaper |
author |
Petrenz‐Beck, Annika Kühn, Jasmin Zuhse, Ralf Ansorge‐Schumacher, Marion B. |
spellingShingle |
Petrenz‐Beck, Annika Kühn, Jasmin Zuhse, Ralf Ansorge‐Schumacher, Marion B. Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application |
author_facet |
Petrenz‐Beck, Annika Kühn, Jasmin Zuhse, Ralf Ansorge‐Schumacher, Marion B. |
author_sort |
Petrenz‐Beck, Annika |
title |
Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application |
title_short |
Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application |
title_full |
Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application |
title_fullStr |
Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application |
title_full_unstemmed |
Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application |
title_sort |
chemo‐enzymatic dynamic kinetic resolution of symmetric and non‐symmetric α‐hydroxy ketones for industrial application |
publisher |
Wiley |
publishDate |
2019 |
url |
http://dx.doi.org/10.1002/slct.201900740 https://onlinelibrary.wiley.com/doi/pdf/10.1002/slct.201900740 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/slct.201900740 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ChemistrySelect volume 4, issue 21, page 6469-6472 ISSN 2365-6549 2365-6549 |
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http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/slct.201900740 |
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ChemistrySelect |
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4 |
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21 |
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6469 |
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6472 |
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1800741675674370048 |