Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids |
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Authors: | Elisabet Selva J. Javier Soto Carmen Nájera Francisco Foubelo José M. Sansano |
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Affiliation: | 1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante 03080, Alicante, Spain;2. Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante 03080, Alicante, Spain;3. Instituto de Síntesis Orgánica, Facultad de Ciencias, Universidad de Alicante 03080, Alicante, Spain;4. Medalchemy, S. L. Avenida Ancha de Castelar, 46 – EA, San Vicente del Raspeig, 03690, Alicante, Spain |
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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. |
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Keywords: | Prolinates Cycloaddition Azomethine ylides Fatty acids Neff reaction |
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