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Highly Stereoselective Oxazaborolidinium Ion Catalyzed Synthesis of (Z)-Silyl Enol Ethers from Alkyl Aryl Ketones and Trimethylsilyldiazomethane

Byung Chul Kang, Su Yong Shim and Do Hyun Ryu*

*Department of Chemistry, Sungkyunkwan University, Suwon, 440-746, Korea, Email: dhryuskku.edu

B. Chul, Kang, S. Y. Shim, D. H. Ryu, Org. Lett., 2014, 16, 2077-2079.

DOI: 10.1021/ol500174q (free Supporting Information)


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Abstract

The use of an oxazaborolidinium ion catalyst enables a highly stereoselective synthesis of (Z)-silyl enol ethers from alkyl aryl ketones and trimethylsilyldiazomethane (TMSD). The conversion of cyclic ketones gives ring-expanded silyl enol ethers.


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Key Words

silyl enol ethers, α-aryl ketones, ring expansion


ID: J54-Y2014