Catalytic Cross-Coupling of Alkylzinc Halides with α-Chloroketones

Chrysa F. Malosh and Joseph M. Ready*
Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038
J. Am. Chem. Soc., 2004, 126 (33), pp 10240–10241
DOI: 10.1021/ja0467768
Publication Date (Web): July 31, 2004
Copyright © 2004 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.

, Joseph.Ready@utsouthwestern.edu

Abstract

Abstract Image

The cross-coupling of alkylzinc halides with α-chloroketones catalyzed by Cu(acac)2 is described. Using this method, primary and secondary alkyl groups are introduced adjacent to a ketone carbonyl under mild reaction conditions and in good yield. Cyclic, acyclic, aromatic, and aliphatic α-chloroketones are suitable substrates. Optically active α-chloroketones are converted to optically active products. The reaction was found to proceed stereospecifically with inversion of stereochemistry. The reaction is proposed to occur by direct substitution of the chloride with the alkyl group of an organocopper, -magnesium, or -zinc species.

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History

  • Published In Issue August 25, 2004
  • Received June 1, 2004

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