On the endo/exo stereoselectivity of intramolecular Diels-Alder reactions of hexadienylacrylates: An interesting failure of density functional theory

Jones, Garth A., Paddon-Row, Michael N., Sherburn, Michael S. and Turner, Craig I. (2002) On the endo/exo stereoselectivity of intramolecular Diels-Alder reactions of hexadienylacrylates: An interesting failure of density functional theory. Organic Letters, 4 (22). pp. 3789-3792. ISSN 1523-7060

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Abstract

A combined experimental and computational study of endo/exo stereoselectivity in a series of IMDA reactions of hexadienylacrylates has found that DFT makes erroneous predictions when the endo and exo transition states possess differing degrees of conjugation. These problems are overcome by carrying out calculations at the MP2 level of theory, which gives remarkably accurate Boltzmann distributions of products. These findings are used to predict ways to obtain either endo- or exo-cycloadducts exclusively.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Light and Energy Faculty of Science > Research Groups > Centre for Photonics and Quantum Science
Depositing User:	Rachel Smith
Date Deposited:	20 Apr 2011 15:08
Last Modified:	28 Mar 2025 04:44
URI:	https://ueaeprints.uea.ac.uk/id/eprint/29764
DOI:	10.1021/ol0264713

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