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Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics

Alexey A Zeifman 1
Alexey A Zeifman
, 
Viktor Sergeevich Stroylov 1
Viktor Sergeevich Stroylov
, 
Ilya Yur'evich Titov 1
Ilya Yur'evich Titov
, 
Fedor Nikolaevich Novikov 1
Fedor Nikolaevich Novikov
, 
Oleg Valentinovich Stroganov 1
Oleg Valentinovich Stroganov
, 
Igor Svitanko 1, 2
Igor Svitanko
, 
Ghermes Grigor'evich Chilov 1
Ghermes Grigor'evich Chilov
10.1016/j.mencom.2015.07.012
Published 2015-07-08
Communication , Volume 25, Issue 4, 269-270
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Zeifman A. A. et al. Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 269-270.
GOST all authors (up to 50) Copy
Zeifman A. A., Stroylov V. S., Titov I. Y., Novikov F. N., Stroganov O. V., Svitanko I., Chilov G. G. Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 269-270.
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TY - JOUR
DO - 10.1016/j.mencom.2015.07.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.012
TI - Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics
T2 - Mendeleev Communications
AU - Zeifman, Alexey A
AU - Stroylov, Viktor Sergeevich
AU - Titov, Ilya Yur'evich
AU - Novikov, Fedor Nikolaevich
AU - Stroganov, Oleg Valentinovich
AU - Svitanko, Igor
AU - Chilov, Ghermes Grigor'evich
PY - 2015
DA - 2015/07/08
PB - Mendeleev Communications
SP - 269-270
IS - 4
VL - 25
ER -
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@article{2015_Zeifman,
author = {Alexey A Zeifman and Viktor Sergeevich Stroylov and Ilya Yur'evich Titov and Fedor Nikolaevich Novikov and Oleg Valentinovich Stroganov and Igor Svitanko and Ghermes Grigor'evich Chilov},
title = {Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.012},
number = {4},
pages = {269--270},
doi = {10.1016/j.mencom.2015.07.012}
}
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Zeifman, Alexey A., et al. “Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics.” Mendeleev Communications, vol. 25, no. 4, Jul. 2015, pp. 269-270. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.012.

Abstract

The enantioselectivity of the Diels–Alder reaction between (E)-3-(4-nitrophenyl)-1-(pyridin-3-yl)prop-2-en-1-one and cyclopenta-1,3-diene in the chiral ionic liquids 3-butyl-1-methylimidazolium (S)-camphorsulfonate and (S)-1-methyl-3-(pyrrolidin-2-ylmethyl)- imidazolium tosylate or upon chiral promotion with chiral oxazaborolidine was modeled by molecular and quantum mechanics and then experimentally studied; computations were in good agreement with the experimental data, resulting in no stereoselectivity with a chiral ionic liquid used as a co-solvent and prominent stereoselectivity upon chiral promotion.

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