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

Filip Colpaert, Sven Mangelinckx UGent, Maria Teresa Rocchetti and Norbert De Kimpe UGent (2011) ORGANIC & BIOMOLECULAR CHEMISTRY. 9(2). p.549-558
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
ASYMMETRIC MICHAEL ADDITION, HALOGENATED IMINO COMPOUNDS, HIGHLY ENANTIOSELECTIVE SYNTHESIS, SALVIA-MILTIORRHIZA, VOLATILE COMPOUNDS, ALDOL REACTIONS, METHYL KETONES, IONIC LIQUID, ALKOXY-KETONES, HYDRAZONE METHOD
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
9
issue
2
pages
549 - 558
Web of Science type
Article
Web of Science id
000285749800032
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.696 (2011)
JCR rank
11/56 (2011)
JCR quartile
1 (2011)
ISSN
1477-0520
DOI
10.1039/c0ob00662a
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1116200
handle
http://hdl.handle.net/1854/LU-1116200
date created
2011-02-02 16:48:51
date last changed
2016-12-19 15:46:29
@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},
  keyword      = {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},
}

Chicago
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.
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.
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.
MLA
Colpaert, Filip, Sven Mangelinckx, Maria Teresa Rocchetti, et al. “New General Synthesis of Alpha-alkoxyketones via Alpha’-alkylation, Alpha-alkylation and Alpha,alpha'-dialkylation of Alpha-alkoxyketimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 9.2 (2011): 549–558. Print.