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Visible‐Light‐Induced Synthesis of 1,2,3,4‐Tetrahydroquinolines through Formal [4+2] Cycloaddition of Acyclic α,β‐Unsaturated Amides and Imides with N , N ‐Dialkylanilines
Author(s) -
Itoh Kennosuke,
Nagao Shunichi,
Tokunaga Ken,
Hirayama Shigeto,
Karaki Fumika,
Mizuguchi Takaaki,
Nagai Kenichiro,
Sato Noriko,
Suzuki Mitsuaki,
Hashimoto Masashi,
Fujii Hideaki
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004186
Subject(s) - cycloaddition , chemistry , stereocenter , imide , photosensitizer , thiourea , combinatorial chemistry , benzothiazine , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
1,2,3,4‐Tetrahydroquinolines should be applicable to the development of new pharmaceutical agents. A facile synthesis of 1,2,3,4‐tetrahydroquinolines that is achieved by a photoinduced formal [4+2] cycloaddition reaction of acyclic α,β‐unsaturated amides and imides with N , N ‐dialkylanilines under visible‐light irradiation, in which a new Ir III complex photosensitizer, a thiourea, and an oxidant act cooperatively in promoting the reaction, is reported. The photoreaction enables the synthesis of a wide variety of 1,2,3,4‐tetrahydroquinolines, while controlling the trans / cis diastereoselectivity (>99:1) and constructing contiguous stereogenic centers. A chemoselective cleavage of an acyclic imide auxiliary is demonstrated.