Development of novel triazole based dendrimer supported spiroborate chiral catalysts for the reduction of (E)-O-benzyl oxime: an enantioselective synthesis of (S)-dapoxetine
| Autor: | Murugesan Sasikumar, Mandapati Bhargava Reddy, Ramasamy Anandhan |
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| Rok vydání: | 2019 |
| Předmět: |
Enantioselective synthesis
Substrate (chemistry) 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology Oxime 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Yield (chemistry) Dendrimer Materials Chemistry Click chemistry 0210 nano-technology Enantiomeric excess |
| Zdroj: | New Journal of Chemistry. 43:15052-15056 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/c9nj03217g |
| Popis: | Novel dendrimer supported spiroborate catalysts 2 and 3 have been synthesized using a click reaction as a key step. The catalytic efficiency of the catalysts have been verified with reduction of (E)-O-benzyl oxime 13 as a model substrate. Catalyst 3 was found to be better than catalyst 2 as the chemical yield and enantiomeric excess were significantly high with the former catalyst. Thus, catalyst 3 has been successfully used in the efficient synthesis of (S)-dapoxetine 14 with 94% ee and 46% overall yield in three steps. These catalysts could be easily recovered from the reaction solution by the solvent precipitation technique and could be reused five times without significant loss of activity and enantioselectivity. |
| Databáze: | OpenAIRE |
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