Advanced search
1 file | 283.18 KB Add to list

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

Author
Organization
Abstract
alpha-Methoxy- and alpha-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 alpha-alkoxyacetone with isopropylamine, and subsequent reaction of the corresponding 1-azaallylic anions with alkyl halides to afford alpha'-alkylated, alpha-alkylated and alpha,alpha'-dialkylated ketimines. Hydrolysis of the imino function led to the desired substituted alpha-alkoxyketones. The ratio of alpha-, alpha'-, and alpha,alpha'-(di)alkylated compounds depended on the amount of base used and on the nature of the alkylating reagent.
Keywords
ASYMMETRIC MICHAEL ADDITION, HALOGENATED IMINO COMPOUNDS, HIGHLY ENANTIOSELECTIVE SYNTHESIS, SALVIA-MILTIORRHIZA, VOLATILE COMPOUNDS, ALDOL REACTIONS, METHYL KETONES, IONIC LIQUID, ALKOXY-KETONES, HYDRAZONE METHOD

Downloads

  • Org. Biomol. Chem. 2011 9 549-558.pdf
    • full text
    • |
    • open access
    • |
    • PDF
    • |
    • 283.18 KB

Citation

Please use this url to cite or link to this publication:

MLA
Colpaert, Filip, et al. “New General Synthesis of Alpha-Alkoxyketones via Alpha’-Alkylation, Alpha-Alkylation and Alpha,Alpha’-Dialkylation of Alpha-Alkoxyketimines.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9, no. 2, 2011, pp. 549–58, doi:10.1039/c0ob00662a.
APA
Colpaert, F., Mangelinckx, S., Rocchetti, M. T., & De Kimpe, N. (2011). New general synthesis of alpha-alkoxyketones via alpha’-alkylation, alpha-alkylation and alpha,alpha’-dialkylation of alpha-alkoxyketimines. ORGANIC & BIOMOLECULAR CHEMISTRY, 9(2), 549–558. https://doi.org/10.1039/c0ob00662a
Chicago author-date
Colpaert, Filip, Sven Mangelinckx, Maria Teresa Rocchetti, and Norbert De Kimpe. 2011. “New General Synthesis of Alpha-Alkoxyketones via Alpha’-Alkylation, Alpha-Alkylation and Alpha,Alpha’-Dialkylation of Alpha-Alkoxyketimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 9 (2): 549–58. https://doi.org/10.1039/c0ob00662a.
Chicago author-date (all authors)
Colpaert, Filip, Sven Mangelinckx, Maria Teresa Rocchetti, and Norbert De Kimpe. 2011. “New General Synthesis of Alpha-Alkoxyketones via Alpha’-Alkylation, Alpha-Alkylation and Alpha,Alpha’-Dialkylation of Alpha-Alkoxyketimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 9 (2): 549–558. doi:10.1039/c0ob00662a.
Vancouver
1.
Colpaert F, Mangelinckx S, Rocchetti MT, De Kimpe N. New general synthesis of alpha-alkoxyketones via alpha’-alkylation, alpha-alkylation and alpha,alpha’-dialkylation of alpha-alkoxyketimines. ORGANIC & BIOMOLECULAR CHEMISTRY. 2011;9(2):549–58.
IEEE
[1]
F. Colpaert, S. Mangelinckx, M. T. Rocchetti, and N. De Kimpe, “New general synthesis of alpha-alkoxyketones via alpha’-alkylation, alpha-alkylation and alpha,alpha’-dialkylation of alpha-alkoxyketimines,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9, no. 2, pp. 549–558, 2011.
@article{1116200,
  abstract     = {{alpha-Methoxy- and alpha-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 alpha-alkoxyacetone with isopropylamine, and subsequent reaction of the corresponding 1-azaallylic anions with alkyl halides to afford alpha'-alkylated, alpha-alkylated and alpha,alpha'-dialkylated ketimines. Hydrolysis of the imino function led to the desired substituted alpha-alkoxyketones. The ratio of alpha-, alpha'-, and alpha,alpha'-(di)alkylated compounds depended on the amount of base used and on the nature of the alkylating reagent.}},
  author       = {{Colpaert, Filip and Mangelinckx, Sven and Rocchetti, Maria Teresa and De Kimpe, Norbert}},
  issn         = {{1477-0520}},
  journal      = {{ORGANIC & BIOMOLECULAR CHEMISTRY}},
  keywords     = {{ASYMMETRIC MICHAEL ADDITION,HALOGENATED IMINO COMPOUNDS,HIGHLY ENANTIOSELECTIVE SYNTHESIS,SALVIA-MILTIORRHIZA,VOLATILE COMPOUNDS,ALDOL REACTIONS,METHYL KETONES,IONIC LIQUID,ALKOXY-KETONES,HYDRAZONE METHOD}},
  language     = {{eng}},
  number       = {{2}},
  pages        = {{549--558}},
  title        = {{New general synthesis of alpha-alkoxyketones via alpha'-alkylation, alpha-alkylation and alpha,alpha'-dialkylation of alpha-alkoxyketimines}},
  url          = {{http://dx.doi.org/10.1039/c0ob00662a}},
  volume       = {{9}},
  year         = {{2011}},
}

Altmetric
View in Altmetric
Web of Science
Times cited: