Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

ABSTRACT: The efficient catalytic activation of donor-acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into cycloadducts in 46-95% yields and up to 95 : 5 diastereomeric ratio using catalytic amounts of triethylsilyl triflimide. Tricyclic indoline frameworks containing four stereogenic centers including all-carbon quaternary centers were obtained.

SUBMITTER: Pirenne V 

PROVIDER: S-EPMC8246098 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature