Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds
Efficient optimization procedures in chiral catalysis are usually linked to a straightforward strategy to access groups of structurally similar catalysts required for fine-tuning. The ease of building up such ligand libraries can be increased when the structure-modifying step (introduction of a subs...
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| Format: | Article |
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MDPI AG
2018-03-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/4/750 |
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| author | Sorachat Tharamak Christian Knittl-Frank Auraya Manaprasertsak Anchulee Pengsook Lydia Suchy Philipp Schuller Barbara Happl Alexander Roller Michael Widhalm |
| author_facet | Sorachat Tharamak Christian Knittl-Frank Auraya Manaprasertsak Anchulee Pengsook Lydia Suchy Philipp Schuller Barbara Happl Alexander Roller Michael Widhalm |
| author_sort | Sorachat Tharamak |
| collection | DOAJ |
| description | Efficient optimization procedures in chiral catalysis are usually linked to a straightforward strategy to access groups of structurally similar catalysts required for fine-tuning. The ease of building up such ligand libraries can be increased when the structure-modifying step (introduction of a substituent) is done at a later stage of the synthesis. This is demonstrated for the extended family of di- and tetranaphtho azepinium compounds, widely used as chiral phase transfer catalysts (PTC). Using 2,6-diiodo-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine and 4,8-diiodo-6,7-dihydro-5H-dibenzo[c,e]azepine, respectively, as key intermediates, 18 spiro-azepinium compounds were synthesized in a total yield of 25–42% over 6–7 steps from 1,1′-binaphthyl-2,2′-dicarboxylic acid or diphenic acid, respectively. The replacement of iodo groups with aryl substituents was performed as the last or the penultimate step of the synthesis. |
| first_indexed | 2024-12-11T08:30:06Z |
| format | Article |
| id | doaj.art-9bab76501a234c81ad7493f721b1f078 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T08:30:06Z |
| publishDate | 2018-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9bab76501a234c81ad7493f721b1f0782022-12-22T01:14:28ZengMDPI AGMolecules1420-30492018-03-0123475010.3390/molecules23040750molecules23040750Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium CompoundsSorachat Tharamak0Christian Knittl-Frank1Auraya Manaprasertsak2Anchulee Pengsook3Lydia Suchy4Philipp Schuller5Barbara Happl6Alexander Roller7Michael Widhalm8Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, Wien 1090, AustriaDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, Wien 1090, AustriaInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, Wien 1090, AustriaInstitute of Inorganic Chemistry, University of Vienna, Währinger Straße 42, Wien 1090, AustriaInstitute of Inorganic Chemistry, University of Vienna, Währinger Straße 42, Wien 1090, AustriaInstitute of Chemical Catalysis, University of Vienna, Währinger Straße 38, Wien 1090, AustriaEfficient optimization procedures in chiral catalysis are usually linked to a straightforward strategy to access groups of structurally similar catalysts required for fine-tuning. The ease of building up such ligand libraries can be increased when the structure-modifying step (introduction of a substituent) is done at a later stage of the synthesis. This is demonstrated for the extended family of di- and tetranaphtho azepinium compounds, widely used as chiral phase transfer catalysts (PTC). Using 2,6-diiodo-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine and 4,8-diiodo-6,7-dihydro-5H-dibenzo[c,e]azepine, respectively, as key intermediates, 18 spiro-azepinium compounds were synthesized in a total yield of 25–42% over 6–7 steps from 1,1′-binaphthyl-2,2′-dicarboxylic acid or diphenic acid, respectively. The replacement of iodo groups with aryl substituents was performed as the last or the penultimate step of the synthesis.http://www.mdpi.com/1420-3049/23/4/7501,1′-binaphthylbiphenylSuzuki-Miyaura couplingphase transfer catalyst |
| spellingShingle | Sorachat Tharamak Christian Knittl-Frank Auraya Manaprasertsak Anchulee Pengsook Lydia Suchy Philipp Schuller Barbara Happl Alexander Roller Michael Widhalm Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds Molecules 1,1′-binaphthyl biphenyl Suzuki-Miyaura coupling phase transfer catalyst |
| title | Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds |
| title_full | Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds |
| title_fullStr | Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds |
| title_full_unstemmed | Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds |
| title_short | Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds |
| title_sort | economy of catalyst synthesis convenient access to libraries of di and tetranaphtho azepinium compounds |
| topic | 1,1′-binaphthyl biphenyl Suzuki-Miyaura coupling phase transfer catalyst |
| url | http://www.mdpi.com/1420-3049/23/4/750 |
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