Stereoselective reduction of chiral trans-3-acetyl-4-alkylpyrrolidin-2-ones |
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| Institution: | 1. Dipartimento di Scienze dei Materiali e della Terra, Università di Ancona, Via Brecce Bianche, I-60131 Ancona, Italy;2. Dipartimento di Scienze Chimiche, Università di Trieste, Via Giorgieri 1, I-34127 Trieste, Italy;1. Organic & Biomolecular Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500 607, India;2. Academy of Scientific and Innovative Research, India;1. Department of Pharmacy, University of Naples “Federico II”, Via D. Montesano, 49, I-80131 Naples, Italy;2. Department of Surgery and Biomedical Sciences, Nuova Facoltà di Medicina, P.zza L. Severi, 1-06132 Perugia, Italy;3. Hospital S. Maria della Misericordia, S. Andrea delle Fratte, 06126 Perugia, Italy;1. Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany;2. Institute of Chemistry, Faculty of Natural Sciences II, University of Halle-Wittenberg, Kurt-Mothes-Strasse 2, D-06120 Halle (Saale), Germany;1. Oceanography Section, Science Research Center, Kochi University, Monobe, Nankoku, Kochi 783-8502, Japan;2. Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu 501-1193, Japan;3. School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan;4. Research Center for Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan;5. Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu, Gifu 501-1193, Japan |
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| Abstract: | A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a–d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a–d and 19a,b with high stereoselection. Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by 1H NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15. |
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