New general synthesis of α-alkoxyketones via α'-alkylation, α-alkylation and α,α'-dialkylation of α-alkoxyketimines

Org Biomol Chem. 2011 Jan 21;9(2):549-58. doi: 10.1039/c0ob00662a. Epub 2010 Oct 26.

Abstract

α-Methoxy- and α-ethoxyketones, as important intermediates in organic synthesis and flavor compounds in food chemistry, were synthesized by deprotonation of N-(1-alkoxy-2-propylidene)isopropylamine, prepared by condensation of the corresponding α-alkoxyacetone with isopropylamine, and subsequent reaction of the corresponding 1-azaallylic anions with alkyl halides to afford α'-alkylated, α-alkylated and α,α'-dialkylated ketimines. Hydrolysis of the imino function led to the desired substituted α-alkoxyketones. The ratio of α-, α'-, and α,α'-(di)alkylated compounds depended on the amount of base used and on the nature of the alkylating reagent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Imines / chemistry*
  • Ketones / chemical synthesis*
  • Molecular Structure
  • Nitriles / chemistry*

Substances

  • Imines
  • Ketones
  • Nitriles
  • ketimine