volume 81 issue 20 pages 10029-10034

Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols

Publication typeJournal Article
Publication date2016-10-04
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
Organic Chemistry
Abstract
A highly efficient method for the selective synthesis of trifluoromethylated morpholines (4-oxa-1-azabicyclo[4.1.0]heptanes) and so far unknown 1,4-oxazepanes (2,8-dioxa-5-azabicyclo[5.1.0]octanes) based on a domino reaction of fluorinated α-bromoenones with β-amino alcohols was elaborated. The assembly of both heterocyclic systems is initiated by an aza-Michael reaction followed by intramolecular cyclization. The conditions for total control of selectivity of the reaction were found.
Found 
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GOST |
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GOST Copy
Rulev A. Y. et al. Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols // Journal of Organic Chemistry. 2016. Vol. 81. No. 20. pp. 10029-10034.
GOST all authors (up to 50) Copy
Rulev A. Y., Romanov A. R., Kondrashov E. V., Ushakov I., Vashchenko A. V., Muzalevskiy V. M., Nenajdenko V. G. Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols // Journal of Organic Chemistry. 2016. Vol. 81. No. 20. pp. 10029-10034.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.joc.6b01927
UR - https://doi.org/10.1021/acs.joc.6b01927
TI - Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols
T2 - Journal of Organic Chemistry
AU - Rulev, Alexander Yu.
AU - Romanov, Alexey R
AU - Kondrashov, Evgeniy V
AU - Ushakov, Igor
AU - Vashchenko, Alexander V.
AU - Muzalevskiy, Vasily M.
AU - Nenajdenko, Valentine G.
PY - 2016
DA - 2016/10/04
PB - American Chemical Society (ACS)
SP - 10029-10034
IS - 20
VL - 81
PMID - 27656759
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2016_Rulev,
author = {Alexander Yu. Rulev and Alexey R Romanov and Evgeniy V Kondrashov and Igor Ushakov and Alexander V. Vashchenko and Vasily M. Muzalevskiy and Valentine G. Nenajdenko},
title = {Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.6b01927},
number = {20},
pages = {10029--10034},
doi = {10.1021/acs.joc.6b01927}
}
MLA
Cite this
MLA Copy
Rulev, Alexander Yu., et al. “Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols.” Journal of Organic Chemistry, vol. 81, no. 20, Oct. 2016, pp. 10029-10034. https://doi.org/10.1021/acs.joc.6b01927.