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Synfacts 2006(6): 0576-0576
DOI: 10.1055/s-2006-934470
DOI: 10.1055/s-2006-934470
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Friedel-Crafts Addition of Indoles to N-Sulfonyl Aldimines
Y.-X. Jia, J.-H. Xie, H.-F. Duan, L.-X. Wang, Q.-L. Zhou*
Nankai UniVersity, P. R. of China
Further Information
Publication History
Publication Date:
19 May 2006 (online)
Significance
This Cu(II)-catalyzed addition of unprotected indoles to N-sulfonyl aldimines provides a simple approach to optically active 3-indolylmethanamine derivatives. This reaction showed remarkable selectivity for the position 3 of the indole. Noteworthy is the reactivity of even sterically demanding substrates (Ar = 2,6-Cl2C6H3: 47%). This reaction is favored for electron-poor aromatic aldimines (EWG = 94%, EDG = 47%).