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Remarkable Effect of N-Substituent on Enantioselective Ruthenium-Catalyzed Propargylation of Indoles with Propargylic Alcohols

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posted on 20.12.2007, 00:00 by Hiroshi Matsuzawa, Keiichiro Kanao, Yoshihiro Miyake, Yoshiaki Nishibayashi
Ruthenium-catalyzed enantioselective propargylation of indoles with propargylic alcohols affords the corresponding β-propargylated indoles in good yields with a high enantioselectivity (up to 95% ee). A remarkable effect of the nature of the N-substituent of indoles is observed for the enantioselectivity of the propargylated indoles. The preparative method described in this paper may provide a novel protocol for asymmetric Friedel−Crafts alkylation of indoles using propargylic alcohols as a new type of electrophiles.