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A Photoredox‐Induced Stereoselective Dearomative Radical (4+2)‐Cyclization/1,4‐Addition Cascade for the Synthesis of Highly Functionalized Hexahydro‐1 H ‐carbazoles
Author(s) -
Alpers Dirk,
Gallhof Malte,
Witt Julian,
Hoffmann Frank,
Brasholz Malte
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201610974
Subject(s) - stereocenter , stereoselectivity , carbazole , indoline , chemistry , radical cyclization , ring (chemistry) , stereochemistry , cascade , total synthesis , combinatorial chemistry , photochemistry , organic chemistry , enantioselective synthesis , catalysis , chromatography
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‐1 H ‐carbazole products are highly valuable intermediates for the synthesis of novel antibiotics, as well as unnatural ring homologues of polycyclic indoline alkaloids.