This article is cited in 5 papers

Communications

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

A. A. Zeifman^a, V. S. Stroylov^a, I. Yu. Titov^a, F. N. Novikov^a, O. V. Stroganov^a, I. Svitanko^ab, G. G. Chilov<sup>a

a</sup> N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation

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.

Language: English

DOI: 10.1016/j.mencom.2015.07.012

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