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Synfacts 2010(5): 0573-0573  
DOI: 10.1055/s-0029-1219636
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tertiary Allylic Ethers by Gold(I) Catalysis

Contributor(s): Hisashi Yamamoto, Kimberly Griffin
M. S. Hadfield, A.-L. Lee*
Heriot-Watt University, Edinburgh, UK
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Alkyl tert-allylic ethers can be regio­selectively formed over traditional primary allylic ethers using a gold(I) complex. DFT studies show isomerization between primary and tertiary ether formation, and the authors use this knowledge to hinder the isomerization process using an excess of alcohol.