Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids

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Title: Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids
Authors: Selva, Elisabet | Soto, J. Javier | Nájera, Carmen | Foubelo, Francisco | Sansano, Jose M.
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Prolinates | Cycloaddition | Azomethine ylides | Fatty acids | N-tert-butylsulfinyl imine | Neff reaction
Knowledge Area: Química Orgánica
Issue Date: 8-Mar-2019
Publisher: Elsevier
Citation: Tetrahedron. 2019, 75(10): 1378-1386. doi:10.1016/j.tet.2019.01.051
Abstract: The α-hydrophobic long chain-α-amino esters are prepared by α-hydroxylation of a series of fatty acid esters [derived from oleic acid (OA), linoleic acid (LA), arachidonic acid (ARA) and docosahexaenoic acid (DHA)] followed by Mitsunobu reaction and hydrazinolysis of the phthalimide. These amino esters are mixed with aldehydes and electrophilic alkenes to give very good chemical yields and diastereoselectivities of prolinate derivatives incorporating a hydrophobic long chain at the α-position. This multicomponent 1,3-dipolar cycloaddition (1,3-DC) takes place at room temperature. The synthesis of the homologue hydrophobic chain of OA is performed by its oxidation to aldehyde/racemic N-tert-butylsulfinyl imine/Neff reaction. Final 1,3-DC with benzaldehyde and N-methylmaleimide affords homologue prolinate derivative in good yield.
Sponsor: We gratefully acknowledge financial support from the Spanish Ministerio Ministerio de Ciencia, Innovación y Universidades (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEOII/2014/017), Medalchemy, S. L. and the University of Alicante. E. S.-M. thanks Medalchemy, S. L./UA for a predoctoral fellowship.
URI: http://hdl.handle.net/10045/88293
ISSN: 0040-4020 (Print) | 1464-5416 (Online)
DOI: 10.1016/j.tet.2019.01.051
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2019 Elsevier Ltd.
Peer Review: si
Publisher version: https://doi.org/10.1016/j.tet.2019.01.051
Appears in Collections:INV - SINTAS - Artículos de Revistas

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