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Synfacts 2008(3): 0269-0269  
DOI: 10.1055/s-2008-1042702
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Ruthenium-Mediated Propargylation of Indoles

Contributor(s): Mark Lautens, Frédéric Ménard
H. Matsuzawa, K. Kanao, Y. Miyake, Y. Nishibayashi*
The University of Tokyo, Japan
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Publication History

Publication Date:
21 February 2008 (online)

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Significance

The above reaction with indoles represents an extension of Nishibayashi’s earlier report for the nucleophilic attack of furans and anilines (Synfacts 2007, 1170). Though a number of methods exist for the propargylation of indoles with Brønsted or Lewis acids, none were reported to be asymmetric. The dimeric ruthenium-thiolate complex is prepared in situ and accomplishes the asymmetric Friedel-Crafts-type alkylation to afford 1,1-disubstituted, unprotected propynes in moderate to good yield and good enantioselectivity.