Artículo
Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis
Autor/es | Herrera González, Irene
Sánchez Fernández, Elena Matilde Sau, Abhijit Nativi, Cristina Garciá Fernández, José M. Galán, M. Carmen Ortiz Mellet, Carmen |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2020 |
Fecha de depósito | 2022-11-30 |
Publicado en |
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Resumen | The first examples of iminosugar-type 2-deoxy(thio)glycoside mimetics are reported. The key step is the activation of a bicyclic iminoglycal carbamate to generate a highly reactive acyliminium cation. Cerium(IV) ammonium ... The first examples of iminosugar-type 2-deoxy(thio)glycoside mimetics are reported. The key step is the activation of a bicyclic iminoglycal carbamate to generate a highly reactive acyliminium cation. Cerium(IV) ammonium nitrate efficiently promoted the formation of 2-deoxy S-glycosides in the presence of thiols, probably by in situ generation of catalytic HNO3, with complete α-stereoselectivity. Cooperative phosphoric acid/Schreiner's thiourea organocatalysis proved better suited for generating 2-deoxy O-glycosides, significantly broadening the scope of the approach. |
Agencias financiadoras | Ministerio de Economía y Competitividad (MINECO). España Ministerio de Ciencia, Innovación y Universidades (MICINN). España European Cooperation in Science and Technology (COST) Consejo Europeo de Investigación |
Identificador del proyecto | SAF201676083-R
RTI2018-097609-B-C21 CA18132 ERC-COG: 648239 |
Cita | Herrera González, I., Sánchez Fernández, E.M., Sau, A., Nativi, C., Garciá Fernández, J.M., Galán, M.C. y Ortiz Mellet, C. (2020). Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis. Journal of Organic Chemistry, 85 (7), 5038-5047. https://doi.org/10.1021/acs.joc.0c00324. |
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Stereoselective Synthesis.pdf | 1.035Mb | [PDF] | Ver/ | |