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Synfacts 2009(6): 0652-0652  
DOI: 10.1055/s-0029-1217197
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rh-Catalyzed Reactions of Ethers Containing Sulfonylacetylenes

Contributor(s): Hisashi Yamamoto, Zhi Li
D. Shikanai, H. Murase, T. Hata, H. Urabe*
Tokyo Institute of Technology, Yokohama, Japan
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

The authors discovered two new reactions of ethers containing sulfonylacetylenes. In dry toluene, benzyl ethers are isomerized to ­dihydropyrans. When water is present in the solvent, the ethers are converted into ketoolefins. As the authors proposed, both reactions undergo the same intermediate to generate their products, ­respectively. The reactions are highly regio- and stereoselective.