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

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

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2015, Volume: 25, Number: 4, Pages: 269-270 Pages count : 2 DOI: 10.1016/j.mencom.2015.07.012

Authors

Zeifman Alexey A. ¹ , Stroylov Viktor S. ¹ , Titov Ilya Yu. ¹ , Novikov Fedor N. ¹ , Stroganov Oleg V. ¹ , Svitanko Igor V. ^1,2 , Chilov Ghermes G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
2	Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation

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.

Zeifman A.A. , Stroylov V.S. , Titov I.Y. , Novikov F.N. , Stroganov O.V. , Svitanko I.V. , Chilov G.G.
Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics
Mendeleev Communications. 2015. V.25. N4. P.269-270. DOI: 10.1016/j.mencom.2015.07.012 WOS Scopus OpenAlex

Web of science:	WOS:000360416600012
Scopus:	2-s2.0-84938688048
OpenAlex:	W1933932091

DB	Citing
OpenAlex	5
Scopus	5
Web of science	5