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Synfacts 2010(12): 1389-1389
DOI: 10.1055/s-0030-1258891
DOI: 10.1055/s-0030-1258891
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Addition of Grignards to Allylic α-Haloacetates
M. Fañanás-Mastral, B. L. Feringa*
University of Groningen, The Netherlands
Further Information
Publication History
Publication Date:
22 November 2010 (online)
Significance
The authors describe a copper-catalyzed allylic substitution of allylic α-chloroacetates 1. While this is the first allylic substitution on these electrophiles, similar substrate classes have also been examined by Trost and Alexakis. This transformation is an alternative strategy to the 1,4-addition of a Grignard reagent to an unsaturated aldehyde; a strategy often marred by competitive 1,2-addition and double additions.
Review: T. Jerphagnon, M. G. Pizzuti, A. J. Minnaard, B. L. Feringa Chem. Soc. Rev. 2009, 38, 1039-1075.