Indium Triflate-Catalyzed Vinylation of β-Ketoesters with Acetylene Gas

Masaharu Nakamura,* Kohei Endo, and Eiichi Nakamura*
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, and PRESTO, Japan Science and Technology Agency, Kawaguchi, Saitama 332-0012, Japan
Org. Lett., 2005, 7 (15), pp 3279–3281
DOI: 10.1021/ol051057z
Publication Date (Web): June 22, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, nakamura@chem.s.u-tokyo.ac.jp

Abstract

Abstract Image

An In(OTf)3-catalyzed addition of a β-ketoester to acetylene in the presence of molecular sieves produces a α-vinylated ketoester in good to excellent yield. The vinylation reaction proceeds without any loss of elements in starting molecules under solvent-free conditions and allows the use of welding-grade acetylene, providing a practical method for synthetic utilization of acetylene gas.

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History

  • Published In Issue July 21, 2005
  • Received May 8, 2005

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