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Synfacts 2007(6): 0609-0609  
DOI: 10.1055/s-2007-968495
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Synthesis of Allylic Aryl Ethers

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. F. Kirsch, L. E. Overman*, N. S. White
University of California, Irvine, USA
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Publikationsdatum:
22. Mai 2007 (online)

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Significance

Generation of highly enantioenriched allylic aryl ethers is described. Using trichloroacetimidates and phenol-type nucleophiles with the [COP-OAc]2 catalyst gives the desired products in high yield with very high ee values. High regioselectivity favoring the branched (chiral) isomer is also obtained, further stating the importance of this procedure. A wide number of Z-al­kenes and variously substituted phenols work very well.