Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles
In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalky...
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MDPI AG
2019-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/18/3405 |
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| author | Jakub Adamek Anna Węgrzyk-Schlieter Klaudia Steć Krzysztof Walczak Karol Erfurt |
| author_facet | Jakub Adamek Anna Węgrzyk-Schlieter Klaudia Steć Krzysztof Walczak Karol Erfurt |
| author_sort | Jakub Adamek |
| collection | DOAJ |
| description | In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and <i>N</i>-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided. |
| first_indexed | 2024-12-10T07:08:42Z |
| format | Article |
| id | doaj.art-8d7e25b904d64eed991a6b9237724d66 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T07:08:42Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8d7e25b904d64eed991a6b9237724d662022-12-22T01:58:06ZengMDPI AGMolecules1420-30492019-09-012418340510.3390/molecules24183405molecules24183405Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus NucleophilesJakub Adamek0Anna Węgrzyk-Schlieter1Klaudia Steć2Krzysztof Walczak3Karol Erfurt4Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandIn this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and <i>N</i>-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.https://www.mdpi.com/1420-3049/24/18/3405organophosphorus chemistryphosphonium saltsphosphonatesphosphinatesphosphine oxides |
| spellingShingle | Jakub Adamek Anna Węgrzyk-Schlieter Klaudia Steć Krzysztof Walczak Karol Erfurt Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles Molecules organophosphorus chemistry phosphonium salts phosphonates phosphinates phosphine oxides |
| title | Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles |
| title_full | Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles |
| title_fullStr | Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles |
| title_full_unstemmed | Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles |
| title_short | Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles |
| title_sort | michaelis arbuzov type reaction of 1 imidoalkyltriarylphosphonium salts with selected phosphorus nucleophiles |
| topic | organophosphorus chemistry phosphonium salts phosphonates phosphinates phosphine oxides |
| url | https://www.mdpi.com/1420-3049/24/18/3405 |
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