Dynamic resolution of 2-cyclohexylidene acetaldehydes through organocatalytic dienamine [4+2] cycloaddition
| Autor: | Tore Kiilerich Johansen, Frank Jensen, Karl Anker Jørgensen, Jakob Blom |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Metals and Alloys Substituent Ether General Chemistry Optically active 010402 general chemistry Dynamic resolution 01 natural sciences Catalysis Cycloaddition 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry.chemical_compound chemistry Yield (chemistry) Materials Chemistry Ceramics and Composites Organic chemistry |
| Zdroj: | Blom, J, Johansen, T K, Jensen, F & Jørgensen, K A 2016, ' Dynamic resolution of 2-cyclohexylidene acetaldehydes through organocatalytic dienamine [4+2] cycloaddition ', Chemical Communications, vol. 52, no. 44, pp. 7153-7156 . https://doi.org/10.1039/c6cc02019d |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c6cc02019d |
| Popis: | Organocatalytic formed dienamines are shown to be involved in dynamic resolution of 2-cyclohexylidene acetaldehydes. By reaction of racemic 2-cyclohexylidene acetaldehydes with benzoquinones in the presence of a diarylprolinol-silyl ether catalyst, tricyclic products are formed in good to high yield and excellent enantioselectivity, while the diastereoselectivity depends on the substituent in the 2-cyclohexylidene acetaldehydes. Studies based on experimental observations and DFT-calculations point to a dynamic thermodynamic resolution-directed pathway. Some transformations of the optically active products are also presented. |
| Databáze: | OpenAIRE |
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