This 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.
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Tandem Catalytic Asymmetric Friedel–Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters†
Article first published online: 2 JUN 2008
DOI: 10.1002/anie.200801373
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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How to Cite
Arai, T. and Yokoyama, N. (2008), Tandem Catalytic Asymmetric Friedel–Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters. Angew. Chem. Int. Ed., 47: 4989–4992. doi: 10.1002/anie.200801373
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Publication History
- Issue published online: 16 JUN 2008
- Article first published online: 2 JUN 2008
- Manuscript Received: 21 MAR 2008
Funded by
- New Energy and Industrial Technology Development Organization (NEDO) of Japan
- Ministry of Education, Culture, Sports, Science and Technology (Japan)
Corrected by:
Corrigendum: Tandem Catalytic Asymmetric Friedel–Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters
Vol. 49, Issue 50, 9555, Article first published online: 7 DEC 2010
Keywords:
- asymmetric catalysis;
- domino reactions;
- Friedel–Crafts reaction;
- Henry reaction;
- multicomponent reactions
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.