C2-Symmetric pyrrolidine-derived squaramides as recyclable organocatalysts for asymmetric Michael reactions

C2-Symmetric pyrrolidine-derived squaramides as recyclable organocatalysts for asymmetric Michael reactions Научная публикация

Журнал

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Вых. Данные

Год: 2016, Том: 14, Номер: 41, Страницы: 9751-9759 Страниц : 9 DOI: 10.1039/c6ob01606e

Авторы

Kucherenko A.S. ¹ , Lisnyak V.G. ¹ , Kostenko A.A. ^1,2 , Kochetkov S.V. ¹ , Zlotin S.G. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russia
2	D. I. Mendeleev University of Chemical Technology, 9 Miusskaya Square, 125047 Moscow, Russia

Novel C2-symmetric N,N′-bis-[(pyrrolidin-2-yl)methyl-squaramide] TFA salts bearing (R,R)- or (S,S)-1,2-di(pyridin-2-yl)ethane spacer groups were synthesized and applied, in combination with TEA, as efficient organocatalysts for asymmetric reactions between cyclohexanone derivatives and β-nitrostyrenes to afford the corresponding Michael adducts in high yields with good to excellent enantioselectivity. The catalytic procedure is readily scalable and recyclable over four times without a negative impact on the selectivity of the reaction. Some of the prepared compounds are valuable precursors to useful bioactive molecules.

Kucherenko A.S. , Lisnyak V.G. , Kostenko A.A. , Kochetkov S.V. , Zlotin S.G.
C2-Symmetric pyrrolidine-derived squaramides as recyclable organocatalysts for asymmetric Michael reactions
Organic & Biomolecular Chemistry. 2016. V.14. N41. P.9751-9759. DOI: 10.1039/c6ob01606e WOS Scopus OpenAlex

Web of science:	WOS:000386670300009
Scopus:	2-s2.0-84992202161
OpenAlex:	W2509589051

БД	Цитирований
OpenAlex	17
Web of science	17
Scopus	18