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Synlett 1997; 1997(6): 731-733
DOI: 10.1055/s-1997-3239
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Excellent Aldehyde and Ketone Selectivity in Chromium(II)-Mediated Reformatsky Reactions

Ludger Wessjohann* , Harry Wild
  • *Institut für Organische Chemie, Ludwig-Maximilians-Universität München, Karlstraße 23, D-80333 München, Germany, Fax +49 (89) 5902-483; E-mail: law@org.chemie.uni-muenchen.de
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Publication Date:
31 December 2000 (online)

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The chromium Reformatsky reaction allows the highly chemoselective addition of ester enolates to aldehydes or methyl ketones at room temperature. Aldehyde selectivities of ≥ 50:1 vs. methyl ketones and ≥ 200:1 vs. larger ketones and other electrophiles can be achieved in most cases. Methyl ketones are preferred with similar effectivity against higher ketones. Effects of solvents, lithium iodide and substituents are discussed.

chemoselectivity - chromium(II) - Reformatsky reaction - Barbier reaction - carbonyl differentiation

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