Stereoselective synthesis of enantiopure γ-aminoalcohols by reduction of chiral β-enaminoketones |
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| Affiliation: | 1. Department of Physics, Haldia Government College, Haldia, Purba Medinipur, 721657, India;2. Université Libre de Bruxelles (ULB), Faculté des Sciences, Laboratoire Chimie des Polymères, CP 206/1, Boulevard du Triomphe, 1050, Bruxelles, Belgium;3. Department of Physics, Uluberia College, Howrah, 711315, India;4. Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, 560 001, India;5. Department of Physics, Jadavpur University, Kolkata, 700032, India;1. Apicore Pharmaceuticals Pvt. Ltd, Block No. 252-253, Dhobikuva Village, Padra-Jambusar Highway, Padra Taluka, Vadodara 391 440, India;2. Department of Chemistry, Amet University, 135, East Coast Road, Kanathur, Chennai 603 112, India;3. Department of Chemistry, Faculty of Science, M. S. University of Baroda, Vadodara 390 002, India;1. Chemistry Department, Faculty of Science, Kuwait University, PO Box 5969, Safat 13060, Kuwait;2. Chemistry Department, Faculty of Science, Fayoum University, Fayoum 63514, Egypt;1. Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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| Abstract: | The results of the reduction of chiral β-enamino ketones with sodium borohydride in acetic acid are reported. The reaction is convenient, stereoselective and high yielding and allows the preparation of enantiopure γ-amino alcohols in syn diastereoselectivity. The reaction is easy to perform and does not require expensive or hazardous chemicals. A mechanistic hypothesis is presented. The absolute configuration of the products obtained is attributed by correlating 1H NMR spectral data with conformational analysis performed by molecular modelling, and confirmed by X-ray analysis. |
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