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Synlett 2000; 2000(2): 257-259
DOI: 10.1055/s-2000-6480
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First Reference to the Alkoxymetallation of Diisobutylaluminium and Bromomagnesium-2-vinyloxy Ethoxide to the Corresponding (1,3-Dioxolan-2-yl)methyl Organometallics

Peter Maier* , Hartmut Redlich
  • *Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Correnstraße 40, D-48149 Münster, Germany; Fax +49 2 51-8 33-97 72; E-mail: redlich@uni-muenster.de
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Publication Date:
31 December 2000 (online)

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Diisobutylaluminium and bromomagnesium-2-vinyloxy-ethoxide add at carbonyl compounds in the manner of (1,3-dioxolan-2-yl)methyl organometallics, giving the carbon-carbon addition products. It is assumed that the aluminium and magnesium compounds of 2-vinyloxy-ethoxide are in equilibrium with the corresponding (1,3-dioxolan-2-yl)methide.

carbanion - intramolecular cyclization - metallation - organometallic reagent - rearrangement

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