An efficient approach to angular tricyclic molecular architecture via Nazarov-like cyclization and double ring-expansion cascade.

ABSTRACT: A modular and efficient method for constructing angular tri-carbocyclic architectures containing quaternary carbon center(s) from 1,3-dicycloalkylidenyl ketones is established, which involves an unconventional synergistic cascade of a Nazarov cyclization and two ring expansions. It features high selectivity, mild conditions and convenient operation, wide scope and easy availability of substrate. Substitution with R¹ and R² at the 4πe-system with electron-donating group favors this reaction, while that with electron-withdrawing group or proton disfavors. The electron-donating group as R¹ directs the initial ring expansion at its own site, while the p-π- or n-π- associated substituent as R² favors selectively the later ring expansion near its locat

SUBMITTER: Wang YP 

PROVIDER: S-EPMC9050659 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature