A highly enantioselective,moderately anti-selective aldol reaction using a novel hydrazone moiety as stereo director |
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| Institution: | 1. Torrey Pines Institute for Molecular Studies, 11350 SW Village Parkway, Port St. Lucie, FL 34987, USA;2. Laboratory of Selective Organic Chemistry & Biological Activity, Faculty of Science of Tunis, University El Manar, 2092, Tunisia;3. Torrey Pines Institute for Molecular Studies, General Atomics Court, San Diego, CA 92121, USA;1. Departamento de Química Inorgánica y Analítica, E.S.C.E.T., Universidad Rey Juan Carlos, 28933 Móstoles, Madrid, Spain;2. Departamento de Química, Universidad del Valle, Calle 13 No 100-00, 76001000 Cali, Colombia;3. Centro de Tecnología Repsol, Autovía de Extremadura A5, km 18, 28935 Móstoles, Madrid, Spain;1. 1st Department of Medicine, University of Szeged, Korányi fasor 8-10, H-6720 Szeged, Hungary;2. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;3. Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary;1. School of Chemistry, The University of New South Wales, Sydney, NSW, 2052, Australia;2. School of Pharmacy, Dicle University, Diyarbakır, 21280, Turkey |
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| Abstract: | The use of novel hydrazones as stereo directors with a view to develop a highly enantioselective, anti-diastereoselective aldol addition procedure has been investigated. A number of proline-derived hydrazones were produced and their effectiveness in directing simple alkylation of aza-enolates investigated. The most promising of these hydrazones were then used in the aldol reaction. The substituent on the oxygen of the proline had a profound effect on both the magnitude and the sense of asymmetric induction. The optimum hydrazone for the formal aldol reaction between pentanone and propionaldehyde gave a diastereoselectivity of 37% in favour of the anti-isomer while both isomers had an ee of 83–84%. |
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