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Lindvall MK, Koskinen AM. Origins of Stereoselectivity in the Corey-Chaykovsky Reaction. Insights from Quantum Chemistry. J Org Chem. 1999;64(13):4596-4606doi: 10.1021/jo9818935.
Lindvall, M. K., & Koskinen, A. M. (1999). Origins of Stereoselectivity in the Corey-Chaykovsky Reaction. Insights from Quantum Chemistry. The Journal of organic chemistry, 64(13), 4596-4606. https://doi.org/10.1021/jo9818935
Lindvall, Mika K., and Koskinen, Ari M. P.. "Origins of Stereoselectivity in the Corey-Chaykovsky Reaction. Insights from Quantum Chemistry." The Journal of organic chemistry vol. 64,13 (1999): 4596-4606. doi: https://doi.org/10.1021/jo9818935
Lindvall MK, Koskinen AM. Origins of Stereoselectivity in the Corey-Chaykovsky Reaction. Insights from Quantum Chemistry. J Org Chem. 1999 Jun 25;64(13):4596-4606. doi: 10.1021/jo9818935. PMID: 11674528.
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J Org Chem. 1999 Jun 25;64(13):4596-4606. doi: 10.1021/jo9818935.

Origins of Stereoselectivity in the Corey-Chaykovsky Reaction. Insights from Quantum Chemistry.

The Journal of organic chemistry

Mika K. Lindvall, Ari M. P. Koskinen

Affiliations

  1. Department of Chemistry, University of Oulu, P.O. Box 3000, FIN-90401 Oulu, Finland.

PMID: 11674528 DOI: 10.1021/jo9818935

Abstract

Reaction pathways of the Corey-Chaykovsky epoxidation reaction have been compared quantum chemically. Of the concerted, torsional rotation and anti addition pathways the latter two were found to be favored both in the gas phase and in CH(2)Cl(2) in a model system. Several theoretically previously uncharacterized stationary points were located, and selective solvent effects were observed. On the anti addition pathway the C-C bond formation transition state A, suitably substituted to allow comparison with published experimental data, was able to predict both the absolute stereochemistry of the main product and, qualitatively, the distribution of its other stereoisomers. The quantum chemical protocol reported here is useful in designing new sulfides for the Corey-Chaykovsky reaction.

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