Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts
The enzyme-catalyzed monoacetylation of prochiral bis (2-hydroxymethylphenyl)methylphosphine and bis (2-hydroxymethylphenyl)phenylphosphine and their <i>P</i>-sulfides gave, in one single step, as a result of desymmetrisation, the corresponding monoacetates in moderate yields and with an...
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MDPI AG
2022-01-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/12/2/171 |
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| author | Lidia Madalińska Piotr Kiełbasiński Małgorzata Kwiatkowska |
| author_facet | Lidia Madalińska Piotr Kiełbasiński Małgorzata Kwiatkowska |
| author_sort | Lidia Madalińska |
| collection | DOAJ |
| description | The enzyme-catalyzed monoacetylation of prochiral bis (2-hydroxymethylphenyl)methylphosphine and bis (2-hydroxymethylphenyl)phenylphosphine and their <i>P</i>-sulfides gave, in one single step, as a result of desymmetrisation, the corresponding monoacetates in moderate yields and with an enantiomeric excess of 16 to 98%, depending on the substrate structure and enzyme applied. The absolute configurations of the selected products were determined by a chemical correlation. This led to the conclusion that, in the case of phosphines, phosphine oxides and phosphine sulfides enzymes preferentially produce compounds of the same spatial arrangement. The new compounds obtained will be transformed into chiral catalysts/ligands. |
| first_indexed | 2024-03-09T22:22:18Z |
| format | Article |
| id | doaj.art-87eec55f4508449887a66e8f2029d97d |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-09T22:22:18Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-87eec55f4508449887a66e8f2029d97d2023-11-23T19:12:24ZengMDPI AGCatalysts2073-43442022-01-0112217110.3390/catal12020171Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral CatalystsLidia Madalińska0Piotr Kiełbasiński1Małgorzata Kwiatkowska2Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandDivision of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandDivision of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandThe enzyme-catalyzed monoacetylation of prochiral bis (2-hydroxymethylphenyl)methylphosphine and bis (2-hydroxymethylphenyl)phenylphosphine and their <i>P</i>-sulfides gave, in one single step, as a result of desymmetrisation, the corresponding monoacetates in moderate yields and with an enantiomeric excess of 16 to 98%, depending on the substrate structure and enzyme applied. The absolute configurations of the selected products were determined by a chemical correlation. This led to the conclusion that, in the case of phosphines, phosphine oxides and phosphine sulfides enzymes preferentially produce compounds of the same spatial arrangement. The new compounds obtained will be transformed into chiral catalysts/ligands.https://www.mdpi.com/2073-4344/12/2/171biotransformationsconfiguration determinationdesymmetrisationenzyme catalysisphosphorus compounds |
| spellingShingle | Lidia Madalińska Piotr Kiełbasiński Małgorzata Kwiatkowska Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts Catalysts biotransformations configuration determination desymmetrisation enzyme catalysis phosphorus compounds |
| title | Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts |
| title_full | Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts |
| title_fullStr | Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts |
| title_full_unstemmed | Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts |
| title_short | Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts |
| title_sort | enzymatic desymmetrisation of prochiral phosphines and phosphine i p i sulfides as a route to i p i chiral catalysts |
| topic | biotransformations configuration determination desymmetrisation enzyme catalysis phosphorus compounds |
| url | https://www.mdpi.com/2073-4344/12/2/171 |
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