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
see article for more reactions
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.
see article for more examples
Key Words
silyl enol ethers, α-aryl ketones, ring expansion
ID: J54-Y2014