4.6 Article

Facile Synthesis of Single α-tert-Alkylated Acetaldehydes by Hydroxyalkylation of Enamides in Aqueous Solution

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 24, Pages 6354-6357

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801099

Keywords

addition; aldehydes; copper; enamides; hydroxyalkylation

Funding

  1. Ube foundation [16K13995]

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In this work, we established a general protocol to synthesize single -tert-alkylated acetaldehydes via Cu-catalyzed hydroxyalkylation of enamides in aqueous solutions. The yields of the products were very high and there was excellent functional group compatibility. Our reaction allows easy access to highly functionalized acetaldehydes that can be used to synthesize further useful compounds including spirocycles. The control experiments revealed that this reaction includes hydroxyalkylation processes via radical reactions.

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