Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid
1
Department of Chemistry, Kyiv Taras Shevchenko University, Volodymyrska Street, 64, Kyiv 01033, Ukraine
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Publication type: Journal Article
Publication date: 2007-06-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A non-chiral, rigid 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, an analogue of 2-aminoadipic acid, has been synthesized in six steps from dimethyl- meso -2,5-dibromohexanedioate in 28% total yield. A key step in the synthesis is double alkylation of a dimethyl pyrrolidine-2,5-dicarboxylate by 1-bromo-2-chloroethane.
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Kubyshkin V., Mikhailiuk P. K., Komarov I. Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid // Tetrahedron Letters. 2007. Vol. 48. No. 23. pp. 4061-4063.
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Kubyshkin V., Mikhailiuk P. K., Komarov I. Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid // Tetrahedron Letters. 2007. Vol. 48. No. 23. pp. 4061-4063.
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TY - JOUR
DO - 10.1016/j.tetlet.2007.04.019
UR - https://doi.org/10.1016/j.tetlet.2007.04.019
TI - Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid
T2 - Tetrahedron Letters
AU - Kubyshkin, Vladimir
AU - Mikhailiuk, Pavel K
AU - Komarov, Igor
PY - 2007
DA - 2007/06/01
PB - Elsevier
SP - 4061-4063
IS - 23
VL - 48
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2007_Kubyshkin,
author = {Vladimir Kubyshkin and Pavel K Mikhailiuk and Igor Komarov},
title = {Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid},
journal = {Tetrahedron Letters},
year = {2007},
volume = {48},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.tetlet.2007.04.019},
number = {23},
pages = {4061--4063},
doi = {10.1016/j.tetlet.2007.04.019}
}
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Kubyshkin, Vladimir, et al. “Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid.” Tetrahedron Letters, vol. 48, no. 23, Jun. 2007, pp. 4061-4063. https://doi.org/10.1016/j.tetlet.2007.04.019.