Additive controlled,stereoselective benzylation of 2-thioxotetrahydropyrimidin-4(1H)-ones via chiral induction from a remote stereocenter |
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Authors: | Varun Kumar Anang Pal Gopal L. Khatik Suman Bhattacharya Vipin A. Nair |
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Affiliation: | 1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, Mohali, Punjab 160 062, India;2. Department of Chemistry, Pondicherry University, Kalapet, Pondicherry 605 014, India |
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Abstract: | Stereoselective alkylation reactions of 3-aryl-1-alkyl-2-thioxotetrahydropyrimidin-4(1H)-one derivatives were studied. The reaction conditions were optimized to obtain the monobenzylated adduct with improved diastereoselectivity by regulating the reaction kinetics using HMPA as the additive and chiral ethyl lactate as the quencher. The absolute configuration of the product was established by NMR experiments, computational calculations, and single crystal X-ray analysis. |
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