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Synfacts 2008(9): 0953-0953
DOI: 10.1055/s-2008-1078663
DOI: 10.1055/s-2008-1078663
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New YorkCu-Catalyzed Tandem Friedel-Crafts/Henry Reaction
Contributor(s):Hisashi Yamamoto, Marina NaodovicT. Arai*, N. Yokoyama
Chiba University, Japan
Tandem Catalytic Asymmetric Friedel-Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters
Angew. Chem. Int. Ed. 2008, 47: 4989-4992
Chiba University, Japan
Tandem Catalytic Asymmetric Friedel-Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters
Angew. Chem. Int. Ed. 2008, 47: 4989-4992
Further Information
Publication History
Publication Date:
22 August 2008 (online)
Key words
copper - tandem reaction - Friedel-Crafts/Henry reaction
Significance
This report describes one of the first successful tandem Friedel-Crafts/Henry (FCH) reactions that provide acyclic chiral products. The most significant point of this account is the predominant formation of only three diastereomers of the three-component reaction products (3) that bear three contiguous stereocenters.
Comment
The authors have shown that the tandem FCH reaction is specific for the copper-imidazoline-amino phenol catalyst (Cu1). The observed syn selectivity, as proposed by the authors, arises from a six-membered transition state in which copper coordinates to two oxygen atoms.