Adv Synth Catal, 2022, 364(9):1587-1595

Chemodivergent Spirocyclization of 2-Sec-Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis

Benzylidene imidazolones with ortho- secondary aminogroup undergo acid-promoted chemodivergent spirocyclization. Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]-hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids promote unprecedented intramolecular umpolung hydroamination reaction with the formation of spirocyclic indolines. Each of the processes proceeds with exclusive atom-economy.

Ivanov DS, Zaitseva ER, Smirnov AY, Rustamova DA, Mikhaylov AA, Sycheva MA, Gluschenko DA, Baleeva NS, Baranov MS

Department of functioning of living systems, Group of chemistry of natural products, Laboratory of chemistry of heterocyclic compounds

: 10.1002/adsc.202200109
Scopus: 2-s2.0-85127606729
IBCH: 9970
Ссылка на статью в журнале: https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200109
Кол-во цитирований на 04.2026: 7
Данные статьи проверены модераторами 2022-04-14

Список научных проектов, где отмечена публикация

  1. -1,5-Гидридный сдвиг в химии гетероциклических соединений: новые структуры, катализаторы и пути применения (July 1, 2020 — June 30, 2025). Baleeva N.S., Smirnov A.Y.. Grant, RSF.