Ruthenium-Catalyzed Enantioselective
Propargylation of Indoles with Propargylic Alcohols

Keiichiro Kanao; Hiroshi Matsuzawa; Yoshihiro Miyake; Yoshiaki Nishibayashi

doi:10.1055/s-0028-1083217

PSP

Ruthenium-Catalyzed Enantioselective Propargylation of Indoles with Propargylic Alcohols

Keiichiro Kanao, Hiroshi Matsuzawa, Yoshihiro Miyake, Yoshiaki Nishibayashi*
Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo 113-8656, Japan
Fax: +81(3)58411175; e-Mail: ynishiba@sogo.t.u-tokyo.ac.jp;

Abstract

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Abstract

Ruthenium-catalyzed enantioselective propargylation of 1-(triisopropylsilyl)-1H-indoles with propargylic alcohols gives the corresponding β-propargylated indoles in good yields with high enantioselectivity. Reactions with 1-(1-naphthyl)prop-2-yn-1-ol achieve the highest enantioselectivity (up to 95% ee).

Key words

asymmetric synthesis - Friedel-Crafts alkylation - ruthenium - indoles - propargylic alcohols

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