Asymmetric Sequential Michael Addition and Cyclization Reactions of 2-(2-Nitrovinyl)phenols Catalyzed by Bifunctional Amino-Squaramides
| Autor: | Radovan Šebesta, Pavlína Molnosiová, Eva Veverková |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Chemistry
Materials Science (miscellaneous) Organic Chemistry Enantioselective synthesis asymmetric catalysis Catalysis Benzopyran Biomaterials michael cyclization reaction chemistry.chemical_compound Yield (chemistry) Organocatalysis Michael reaction Organic chemistry organocatalysis Phenols Bifunctional QD1-999 amino-squaramides |
| Zdroj: | SynOpen, Vol 05, Iss 04, Pp 278-284 (2021) |
| ISSN: | 2509-9396 |
| DOI: | 10.1055/s-0040-1719843 |
| Popis: | In this work, we describe the Michael addition–cyclization reaction of 2-(2-nitrovinyl)phenol with two different reactive Michael donors, which lead to chiral benzopyran derivatives. Specifically, bifunctional amino-squaramides with one or two chiral units in the side chains were evaluated as catalysts in these transformations. Furthermore, the utility of selected green solvents as reaction media for these processes was also tested. The best result was achieved with methyl-cyclopentanone-2-carboxylate as the Michael donor in ethyl (–)-l-lactate with quinine-based amino-squaramide as catalyst (yield 72%, dr >99:1, ee 99%). |
| Databáze: | OpenAIRE |
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