Chem. J. Chinese Universities ›› 2009, Vol. 30 ›› Issue (12): 2400.

• Articles • Previous Articles     Next Articles

Convenient Asymmetric Direct α-Phenylethynylation of β-Dicarbonyl Compounds

ZHU Min*, LI Li, SUN Na-Bo, LI He   

  1. College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, China
  • Received:2009-02-25 Online:2009-12-10 Published:2009-12-10
  • Contact: ZHU Min. E-mail: hzzm60@163.com
  • Supported by:

    国家自然科学基金(批准号: 20672100)资助.

Abstract:

A novel chiral alkynyliodonium salt, phenyl(phenylethynyl)iodonium(10-camphorsulfonate) was prepared by simply stirring of phenylacetylene with [hydroxyl-(((+)-10-camphorsulfonyl)oxy)iodo]benzene in CHCl3 overnight at room temperature. The asymmetric reaction with enolate anions of β-dicarbonyl compounds was studied in t-BuOH at room temperature, which gave good yields of α-phenylethynylated products with moderate values of e.e. value. The method for asymmetric direct α-phenylethynylation of β-dicarbonyl compounds was first reported, which had some advantages such as mild reaction conditions, simple procedure and with moderate values of e.e. value. Furthermore, the scope of hypervalent iodine compounds in asymmetric organic synthesis could be extended.

Key words: Chiral hypervalentiodonium salt; Phenyl(phenylethynyl)iodonium(10-camphorsulfonate); Asymmetric α-phenylethynylation of β-dicarbonyl compound

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