Enantioselective synthesis of unsaturated amino acids using p-methoxybenzylamine as an ammonia equivalent |
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| Affiliation: | 1. Laboratorio de Síntesis Orgánica, Departamento de Química Orgánica, Facultad de Química—Universidad de la República, General Flores 2124, 11800 Montevideo, Uruguay;2. Cryssmat-Lab, Cátedra de Física, DETEMA., Facultad de Química—Universidad de la República, General Flores 2124, 11800 Montevideo, Uruguay;1. Leibniz-Institut für Katalyse an der Universität Rostock e.V, Albert-Einstein-Str. 29a, 18059 Rostock, Germany;2. Department of Chemistry, Zhejiang Sci-Tech University, Xiasha Campus, Hangzhou 310018, People''s Republic of China;1. Global Discovery Chemistry, Novartis Institutes for BioMedical Research, 250 Massachusetts Avenue, Cambridge, MA 02139, United States;2. Cardiovascular and Metabolism, Novartis Institutes for BioMedical Research, 100 Technology Square, Cambridge, MA 02139, United States;1. TOS Department, Ural Federal University named after the first President of Russia B.N. Yeltsin, 620002, 19 Mira Str., Yekaterinburg, Russia;2. Medical University of Vienna, Department of Pediatrics, 1090, 14 Lazarettgasse, Vienna, Austria;3. I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, 20 S. Kovalevskaya Str., 620990 Ekaterinburg, Russia;4. Klinik für Allgemein-und Viszeralchirurgie Zentrum für Chirurgie Universitätsklinikum Ulm, 23 Albert-Einstein-Allee, 89081 Ulm, Germany;5. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium |
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| Abstract: | ![]()
A versatile, non-alkylative enantioselective synthesis of unsaturated α-amino acids based on the Sharpless asymmetric epoxidation has been developed. Enantiomerically enriched trans epoxy alcohols bearing unsaturated substituents were prepared and submitted to regio- and stereospecific ring-opening with p-methoxybenzylamine as a nucleophile, leading to anti-3-(p-methoxybenzylamino)-1,2-diols which were further protected by reaction with Boc2O. The 1,2-diol fragment was then oxidatively cleaved by a sequential treatment with sodium periodate and sodium chlorite to afford the corresponding amino acid. Using this methodology, doubly N-protected (p-methoxybenzyl and Boc) allyl glycine, 3-butenyl glycine and 4-pentenyl glycine have been prepared in three synthetic steps from the corresponding allyl alcohols. As a demonstration of the orthogonal nature of the nitrogen protection, both protecting groups have been selectively removed from the fully protected amino ester. |
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