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Mild and Efficient Pentafluorophenylammonium Triflate (PFPAT)-Catalyzed C-Acylations of Enol Silyl Ethers or Ketene Silyl (Thio)Acetals with Acid Chlorides

Akira Iida, Jun Osada, Ryohei Nagase, Tomonori Misaki and Yoo Tanabe*

*Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan, Email: tanabekwansei.ac.jp

A. Iida, J. Osada, R. Nagase, T. Misaki, Y. Tanabe, Org. Lett., 2007, 9, 1859-1862.

DOI: 10.1021/ol070191b (free Supporting Information)


Abstract

Pentafluorophenylammonium triflate (PFPAT) successfully catalyzed the C-acylation of enol silyl ethers with acid chloride to produce various β-diketones in good yield. Similarly, C-acylation of ketene silyl acetals or ketene silyl thioacetals proceeded smoothly to provide also thermodynamically unfavorable α,α-dialkylated β-keto (thio)esters in good yield.

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Powerful Ti-Crossed Claisen Condensation between Ketene Silyl Acetals or Thioacetals and Acid Chlorides or Acids

A. Iida, S. Nakazawa, T. Okabayashi, A. Horii, T. Misaki, Y. Tanabe, Org. Lett., 2006, 8, 5215-5218.


Key Words

Claisen Condensation, Diketones, Ketocarboxylic Esters, Thioesters


ID: J54-Y2007-1350