Synthesis 2008(23): 3869-3873  
DOI: 10.1055/s-0028-1083217
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

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;
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Publikationsverlauf

Received 28 July 2008
Publikationsdatum:
06. November 2008 (online)

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).