Synthesis of five-, six-, and seven-membered ring lactams by CpRh complex-catalyzed oxidative N-heterocyclization of amino alcohols

Ken-ichi Fujita; Yoshinori Takahashi; Maki Owaki; Kazunari Yamamoto; Ryohei Yamaguchi

doi:10.1021/ol0489954

Synthesis of five-, six-, and seven-membered ring lactams by CpRh complex-catalyzed oxidative N-heterocyclization of amino alcohols

Org Lett. 2004 Aug 5;6(16):2785-8. doi: 10.1021/ol0489954.

Authors

Ken-ichi Fujita¹, Yoshinori Takahashi, Maki Owaki, Kazunari Yamamoto, Ryohei Yamaguchi

Affiliation

¹ Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan. fujitak@kagaku.mbox.media.kyoto-u.ac.jp

PMID: 15281769
DOI: 10.1021/ol0489954

Abstract

A new effective catalytic system consisting of [CpRhCl(2)](2)/K(2)CO(3) (Cp = pentamethylcyclopentadienyl) for the lactamization of amino alcohols has been developed. As an example, the reaction of 3-(2-aminophenyl)-1-propanol in the presence of [CpRhCl(2)](2) (5.0% Rh) and K(2)CO(3) (10%) in acetone gives 3,4-dihydro-2(1H)-quinolinone in an isolated yield of 80%. A variety of five-, six-, and seven-membered benzo-fused lactams are synthesized by this catalytic system. [reaction: see text]