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Synthesis 1997; 1997(5): 512-514
DOI: 10.1055/s-1997-1219
short paper
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The Chromium Reformatsky Reaction: Acces to Adjacent Quarternary Centers

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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Publikationsdatum:
31. Dezember 2000 (online)

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α-Bromo ketones, -esters and -nitriles react with chromium dichloride and ketones in a Barbier-type reaction to yield the kinetic crossed aldol products with one or two new quarternary centers. The reaction does not require special activation of the reagent, proceeds at room temperature and is suitable for microscale preparations. Crotonates react highly regioselective to yield α-products. The influence of solvents is discussed.

Reformatsky reaction - Barbier reaction - quarternary centers - chromium(II) chloride - crotonate regio- and diastereoselectivity