title: A Photoredox-Induced Stereoselective Dearomative Radical (4+2)-Cyclization/1,4-Addition Cascade for the Synthesis of Highly Functionalized Hexahydro-1H-carbazoles.
abstract: A stereoselective synthesis of functionalized hexahydrocarbazoles was developed based on an unprecedented photoredox-induced dearomative radical (4+2)-cyclization/1,4-addition cascade between 3-(2-iodoethyl)indoles and acceptor-substituted alkenes. The title reaction simultaneously generates three C-C bonds and one C-H bond, along with three contiguous stereogenic centers. The hexahydro-1H-carbazole products are highly valuable intermediates for the synthesis of novel antibiotics, as well as unnatural ring homologues of polycyclic indoline alkaloids.
authors.affiliation: Department of Chemistry-Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
authors.forename: Dirk
authors.initials: D
authors.lastname: Alpers
authors.affiliation: Department of Chemistry-Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
authors.forename: Malte
authors.initials: M
authors.lastname: Gallhof
authors.affiliation: Department of Chemistry-Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
authors.forename: Julian
authors.initials: J
authors.lastname: Witt
authors.affiliation: Department of Chemistry-Institute of Inorganic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Hoffmann
authors.affiliation: Department of Chemistry-Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
authors.forename: Malte
authors.identifier: 0000-0001-8184-646X
authors.initials: M
authors.lastname: Brasholz
keywords: carbazoles; cascade reactions; indolines; photocatalysis; radicals