Tandem Catalytic Asymmetric Friedel–Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters†
Correction(s) for this article
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Tandem Catalytic Asymmetric Friedel–Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters
- Volume 49Issue 50Angewandte Chemie International Edition
- pages: 9555-9555
- First Published online: December 7, 2010
Takayoshi Arai Prof. Dr.
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522 (Japan), Fax: (+81) 43-290-2889 http://synthesis.chem.chiba-u.jp/
Search for more papers by this authorNaota Yokoyama
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522 (Japan), Fax: (+81) 43-290-2889 http://synthesis.chem.chiba-u.jp/
Search for more papers by this authorTakayoshi Arai Prof. Dr.
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522 (Japan), Fax: (+81) 43-290-2889 http://synthesis.chem.chiba-u.jp/
Search for more papers by this authorNaota Yokoyama
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522 (Japan), Fax: (+81) 43-290-2889 http://synthesis.chem.chiba-u.jp/
Search for more papers by this authorThis research was supported by the Industrial Technology Research Grant Program in 2006 from the New Energy and Industrial Technology Development Organization (NEDO) of Japan and by a Grant-in Aid for Scientific Research on Priority Areas (No. 19028007, “Chemistry of Concerto Catalysis”) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We thank Prof. Akira Yanagisawa at Chiba University for helpful discussions.
Graphical Abstract
Good things come in threes: Highly functionalized indole derivatives with three contiguous stereocenters were formed in the title reaction of an indole, a nitroalkene, and an aldehyde with the imidazoline–aminophenol catalyst 1–CuOTf in the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The major isomers of the adducts were obtained with up to 99 % ee. Tf=trifluoromethanesulfonyl, Ts=p-toluenesulfonyl; R=H, Me; R′,R′′=alkyl, aryl.
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