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Synfacts 2008(7): 0717-0717  
DOI: 10.1055/s-2008-1077842
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Friedel-Crafts-Type Allylic Alkylation of Indoles

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
W. B. Liu, H. He, L. X. Dai, S. L. You*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

Using a Mo(II) catalyst system, Ko¡covsk first reported the non-enantioselective allylic alkylation of various electron-rich aromatics and hetero-aromatics with allyl acetates (J. Org. Chem. 1999, 64, 2751). Subsequently, several reports of enantioselective versions using Pd have appeared. In the present study, the authors disclose the first iridium-catalyzed allylic alkylation of indole with unsymmetrical aromatic and aliphatic allyl carbonates to afford branched Friedel-Crafts-type products in high yields and enantioselectivities.