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Additive controlled, stereoselective benzylation of 2-thioxotetrahydropyrimidin-4(1H)-ones by chiral induction from a remote stereocentre

Publication Type : Journal Article

Publisher : Elsevier

Source : Tetrahedron: Asymmetry, 2012

Url : https://www.sciencedirect.com/science/article/pii/S0957416612001929?casa_token=hHw5nI2AE84AAAAA:Li2er34Hw5RAcU17VE94_19P_rgda9Llnch5MeRc17r_0uv3fWg3e2wm4yO-3ipul5mPSKsmCHE

Campus : Amritapuri

School : School of Biotechnology

Verified : No

Year : 2012

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.

Cite this Research Publication : Varun Kumar, Anang Pal, Gopal L. Khatik, Suman Bhattacharya and Vipin A. Nair, "Additive controlled, stereoselective benzylation of 2-thioxotetrahydropyrimidin-4(1H)-ones by
chiral induction from a remote stereocentre", Tetrahedron: Asymmetry, 2012, 23, 434-442

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