Oxidative cyclization of amino alcohols catalyzed by a CpIr complex. Synthesis of indoles, 1,2,3,4-tetrahydroquinolines, and 2,3,4,5-tetrahydro-1-benzazepine

Ken-Ichi Fujita; Kazunari Yamamoto; Ryohei Yamaguchi

doi:10.1021/ol026200s

Oxidative cyclization of amino alcohols catalyzed by a CpIr complex. Synthesis of indoles, 1,2,3,4-tetrahydroquinolines, and 2,3,4,5-tetrahydro-1-benzazepine

Org Lett. 2002 Aug 8;4(16):2691-4. doi: 10.1021/ol026200s.

Authors

Ken-Ichi Fujita¹, Kazunari Yamamoto, Ryohei Yamaguchi

Affiliation

¹ Department of Natural Resources, Graduate School of Global Environmental Studies, Kyoto University, Japan. fujitak@kagaku.h.kyoto-u.ac.jp

PMID: 12153211
DOI: 10.1021/ol026200s

Abstract

[reaction: see text] A new iridium-catalyzed oxidative cyclization of amino alcohols has been revealed. Indole derivatives are synthesized in good to excellent yields from 2-aminophenethyl alcohols by means of a [CpIrCl(2)](2)/K(2)CO(3) catalytic system. The present catalytic system is also effective for syntheses of 1,2,3,4-tetrahydroquinolines from 3-(2-aminophenyl)propanols and 2,3,4,5-tetrahydro-1-benzazepine from 4-(2-aminophenyl)butanol.