Copper Complex of Pinene based Schiff base [CuSBADBH] 2 : Synthesis and its Application in Catalytic Asymmetric Nitroaldol (Henry) Reaction
| Autor: | You-Ming Chang, Gene-Hsian Lee, Chinpiao Chen, Ramalingam Boobalan |
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| Rok vydání: | 2016 |
| Předmět: |
Pinene
Copper complex Nitroaldol reaction Schiff base 010405 organic chemistry Enantioselective synthesis chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Copper 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Yield (chemistry) Organic chemistry |
| Zdroj: | ChemistrySelect. 1:2028-2034 |
| ISSN: | 2365-6549 |
| DOI: | 10.1002/slct.201600359 |
| Popis: | Eight new pinene based tridentate Schiff bases of (+)-(1S,2R,3S,5S)-3-amino-6,6-dimethylbicyclo[3.1.1]heptan-2-ol were synthesized from (+)-(α)-pinene. Copper complexes of these Schiff bases were prepared for asymmetric nitroaldol (Henry) reaction. Among the eight copper complexes, 3-methylsalicylaldehyde-derived [CuSBADBH-4]2 32 showed high chiral induction (85 % ee) for the catalytic asymmetric Henry reaction of 4-nitrobenzaldehyde. Under optimal reaction conditions, 1 mol% [CuSBADBH-4]2 32 catalyzed enantioselective Henry reaction of various aromatic and poly aromatic aldehydes afforded the corresponding (R)-β-hydroxy nitroalkanes with high ee (up to 92 %) and yield (up to 99 %). |
| Databáze: | OpenAIRE |
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