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

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dc.contributorSíntesis Asimétrica (SINTAS)es_ES
dc.contributor.authorSelva, Elisabet-
dc.contributor.authorSoto, J. Javier-
dc.contributor.authorNájera, Carmen-
dc.contributor.authorFoubelo, Francisco-
dc.contributor.authorSansano, Jose M.-
dc.contributor.otherUniversidad de Alicante. Departamento de Química Orgánicaes_ES
dc.contributor.otherUniversidad de Alicante. Instituto Universitario de Síntesis Orgánicaes_ES
dc.identifier.citationTetrahedron. 2019, 75(10): 1378-1386. doi:10.1016/j.tet.2019.01.051es_ES
dc.identifier.issn0040-4020 (Print)-
dc.identifier.issn1464-5416 (Online)-
dc.description.abstractThe 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.es_ES
dc.description.sponsorshipWe 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.es_ES
dc.rights© 2019 Elsevier Ltd.es_ES
dc.subjectAzomethine ylideses_ES
dc.subjectFatty acidses_ES
dc.subjectN-tert-butylsulfinyl iminees_ES
dc.subjectNeff reactiones_ES
dc.subject.otherQuímica Orgánicaes_ES
dc.titleProline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acidses_ES
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