Реферат: The idea of (3 + 2)-construction of pyrrolidines is realized based on a common natural substrate modified at a single position by functional groups with opposite electronic effects. Their role in switching the diastereoselectivity mode of cycloaddition is shown for the first time. In this work, Lewis-acid-complexcatalyzed (3 + 2)-cycloaddition reactions involving donor–acceptor cyclopropanes (DACs) and newly obtained citral imines were investigated and optimized. Based on the results obtained, a method for the diastereoselective synthesis of substituted 2,5-cis- and trans-pyrrolidines was developed. Our approach demonstrates broad substrate scope and significant synthetic utility, as evidenced by the directed product derivatization. This work expands the applicability of the known method to a wider range of aliphatic substrates due to the decisive participation of Yb(NTf2)3/PyBOX as a catalyst.

Библиографическая ссылка: Sergeev P.G. , Novikov R.A. , Tomilov Y.V.
Stereodivergent (3 + 2)-cycloaddition of donor–acceptor cyclopropanes and citral imines catalyzed by Yb(NTf 2 ) 3 /PyBOX
Organic & Biomolecular Chemistry. 2026. DOI: 10.1039/d6ob00121a WOS Scopus OpenAlex

Даты:

Поступила в редакцию:	22 янв. 2026 г.
Принята к публикации:	5 мар. 2026 г.
Опубликована в печати:	5 мар. 2026 г.

Идентификаторы БД:

≡ Web of science:	WOS:001721217300001
≡ Scopus:	2-s2.0-105033804421
≡ OpenAlex:	W7133752018

Альметрики: