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Theoretical analysis of the regio- and stereoselective synthesis of spiroisoxazolines

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Abstract

The [3+2] cycloaddition (32CA) reaction of benzonitrile oxide to α-methylene cyclopentanone and propionitrile oxide to γ-methyl-α-methylene-γ-butyrolactone, yielding regio- and stereochemically defined spiroisoxazolines, has been studied at the MPWB1K/6-311G(d,p) computational level. These processes proceed by a one-step mechanism through asynchronous transition states. Ortho regioselectivity and anti diastereofacial selectivity are predicted in complete agreement with the experimental outcomes.

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Acknowledgments

The author is thankful to Professor Manas Banerjee, Retired Professor, at The University of Burdwan, India, for his kind cooperation. The author also acknowledges the help and support of Professor Luis R Domingo, Professor, at the University of Valencia, Spain, for important clarifications in several studies related to the concept of 32CA reactions.

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  1. Department of Chemistry, Durgapur Government College, Durgapur, Paschim Bardhaman, West Bengal, 713214, India

    Nivedita Acharjee

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ESM 1

Tables with the MPWB1K/6-311G(d,p) electronic energies, enthalpies and Gibbs free energies of the stationary points involved in the 32CA reactions of nitrile oxides 1 and 4 with MCP 2 and MBL 5, in gas phase, THF and benzene. ELF topological analysis at the reactants and TSs and calculations of QTAIM parameters. (DOCX 1124 kb).

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Acharjee, N. Theoretical analysis of the regio- and stereoselective synthesis of spiroisoxazolines. J Mol Model 26, 117 (2020). https://doi.org/10.1007/s00894-020-04372-x

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