Kennosuke Itoh, Shun‐ichi Nagao, K. Tokunaga
Dec 10, 2020
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Influential Citations
4
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Journal
Chemistry
Abstract
1,2,3,4-Tetrahydroquinolines should be applicable to the development of novel pharmaceutical agents. We report a facile synthesis of 1,2,3,4-tetrahydroquinolines that was achieved by a photo-induced formal [4+2] cycloaddition reaction of acyclic α,β-unsaturated amides and imides with N,N-dialkylanilines under visible-light irradiation where a novel Ir(III) complex photo-sensitizer, a thiourea, and an oxidant act cooperatively in promoting the reaction. The photo-reaction enables the synthesis of a wide variety of 1,2,3,4-tetrahydroquinolines while controlling trans/cis diastereoselectivity (>99:1) and constructing contiguous stereogenic centers . A chemoselective cleavage of an acyclic imide auxiliary is demonstrated .