Visible-Light-Induced Enantioselective Dearomative [2+2]-Cycloaddition/Ring-Expansion Sequence of Indoles with Simple Alkenes

Abstract

Catalytic asymmetric dearomatization reactions represent a versatile platform for constructing complex optically active three-dimensional molecules. We present a visible-light-induced asymmetric dearomative [2+2] cycloaddition/ring-expansion reaction of indole derivatives with simple alkenes in the presence of a chiral N,N′-dioxide/terbium complex. This strategy provides access to a range of valuable cyclopenta[b]indoles, and its synthetic potential is further showcased through a gram-scale synthesis, potential bioactivity against human breast cancer, and further transformation into a yuehchukene analogue. A series of control and spectral experiments, as well as DFT calculations, provide compelling evidence to elucidate the reaction mechanism.

Key words

dearomatization - photocatalysis - indoles - asymmetric catalysis - [2+2] photocycloaddition - cyclopentaindolones

Publikationsverlauf

Eingereicht: 18. September 2024

Angenommen nach Revision: 03. Dezember 2024

Artikel online veröffentlicht:
28. Januar 2025

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