C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions Научная публикация
| Журнал |
Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263 |
||
|---|---|---|---|
| Вых. Данные | Год: 2019, Том: 84, Номер: 7, Страницы: 4304-4311 Страниц : 8 DOI: 10.1021/acs.joc.9b00252 | ||
| Авторы |
|
||
| Организации |
|
Реферат:
A very simple and highly efficient C2-symmetric tertiary amine-squaramide organocatalyst for asymmetric Michael reactions has been elaborated. In the presence of only 1 mol % of this catalyst, kojic acid derivatives and β-dicarbonyl compounds reacted with nitroolefins, affording the corresponding adducts in a nearly quantitative yield with an enantioselectivity up to 99% ee. The kojic acid-derived adducts could be efficiently produced under “green” conditions (in 96% EtOH or pure water). Moreover, due to the very low solubility in organic solvents, the developed nonsupported catalyst could be readily recovered and reused in catalytic reactions up to 7 times. Utmost availability (one-step synthesis without chromatographic purification), high level of stereoinduction, low efficient loading, and recyclability make it attractive for industrial application in the pharmaceutical industry.
Библиографическая ссылка:
Kucherenko A.S.
, Kostenko A.A.
, Komogortsev A.N.
, Lichitsky B.V.
, Fedotov M.Y.
, Zlotin S.G.
C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
Journal of Organic Chemistry. 2019. V.84. N7. P.4304-4311. DOI: 10.1021/acs.joc.9b00252 WOS Scopus OpenAlex
C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
Journal of Organic Chemistry. 2019. V.84. N7. P.4304-4311. DOI: 10.1021/acs.joc.9b00252 WOS Scopus OpenAlex
Идентификаторы БД:
| Web of science: | WOS:000464250800053 |
| Scopus: | 2-s2.0-85063127206 |
| OpenAlex: | W2920792191 |