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Issue 6, 1997

Sulfur-controlled 5-exo selective aryl radical cyclisation of N-vinylic 2-bromobenzamides: synthesis of lennoxamine and chilenine

Abstract

Bu3SnH-mediated aryl radical cyclisation of N-[2,2-bis(phenylsulfanyl)ethenyl]-2-bromobenzamides 12a–d and 16 takes place in a 5-exo manner to give exclusively the isoindolones 15a–d and 17, respectively. The isoindolone 17 is converted into lennoxamine and a key intermediate 20 for the synthesis of chilenine.

Article information


J. Chem. Soc., Perkin Trans. 1, 1997, 817-822
Article type
Paper

Sulfur-controlled 5-exo selective aryl radical cyclisation of N-vinylic 2-bromobenzamides: synthesis of lennoxamine and chilenine

H. Ishibashi, H. Kawanami and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1997, 817 DOI: 10.1039/A606723I

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