- New general synthesis of α-alkoxyketones via α′- alkylation, α-alkylation and α,α′-dialkylation of α-alkoxyketimines
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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.
- Colpaert, Filip,Mangelinckx, Sven,Rocchetti, Maria Teresa,De Kimpe, Norbert
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experimental part
p. 549 - 558
(2011/02/28)
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