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Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands

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Abstract

Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF3 group.

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ACKNOWLEDGMENTS

The research was financially supported by the Scientific Research Commission of the Hatay Mustafa Kemal University (Grant No. 08F0201 and Grant no. 1005M0115).

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  1. Department of Chemistry, Arts and Science Faculty, Hatay Mustafa Kemal University, 31040, Antakya, Turkey

    A. E. Aydin

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Aydin, A.E. Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands. Russ J Org Chem 56, 901–909 (2020). https://doi.org/10.1134/S1070428020050255

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