Article
Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines
Author/s | Elías Rodríguez, María del Pilar
Carmona Asenjo, Ana Teresa Moreno Vargas, Antonio José Robina Ramírez, Inmaculada |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2022 |
Deposit Date | 2023-05-12 |
Published in |
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Abstract | Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The ... Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and diastereoselectivities but with moderate enantiocontrol. The stereochemical outcome of the reaction depends on the substituent at the nitrogen atom and hydroxyl groups, the configuration of the stereogenic centers and the distance between the diphenylphosphine group and the pyrrolidine skeleton of the catalyst. The preparation of both enantiomers of the catalyst allowed the corresponding enantiomeric pyrrolines to be obtained with similar yields, diastereo- and enantioselectivities. |
Funding agencies | Ministerio de Ciencia e Innovación (MICIN). España Junta de Andalucía |
Project ID. | CTQ2016–77270-R
PID2020-116460RB-100 FQM-345 |
Citation | Elías Rodríguez, M.d.P., Carmona Asenjo, A.T., Moreno Vargas, A.J. y Robina Ramírez, I. (2022). Iminosugar-Phosphines as Organocatalysts in the [3 + 2] Cycloaddition of Allenoates and N-Tosylimines. Catalysts, 12 (8). https://doi.org/10.3390/catal12080876. |
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