@article{667243de69294ec1b273e065e90ef85f,
title = "Theoretical Analysis of the Heterocyclic [4+2] Cycloaddition Between Pyridinium Ion and Enol Ether",
abstract = "Dearomative heterocyclic [4+2] cycloaddition between the N-(2,4-dinitrophenyl)pyridinium ion of nicotinamide and an enol ether was analyzed by Density Functional Theory (DFT) calculations. The calculation revealed that the reaction undergoes stepwise bond formation rather than occurring in a concerted manner. The experimental products were found to be both kinetically and thermodynamically favored. The calculated transition states and intermediate suggested that the high diastereoselectivity is derived from the electrostatic interaction between the 2-nitro group of the pyridinium ion and the hydrogen of the enol ether.",
keywords = "[4+2] cycloaddition, density functional theory, pyridinium, reaction mechanism, stepwise",
author = "Masataka Nakahara and Kengo Hanaya and Takeshi Sugai and Shuhei Higashibayashi",
note = "Funding Information: This work was supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant No. 20K05499 (S.H.). Part of the calculations was performed using Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: {\textcopyright} 2021 The Authors. Published by Wiley-VCH GmbH",
year = "2021",
month = jun,
doi = "10.1002/open.202000310",
language = "English",
volume = "10",
pages = "627--629",
journal = "ChemistryOpen",
issn = "2191-1363",
publisher = "John Wiley and Sons Inc.",
number = "6",
}