Focusing on Organocatalytic Asymmetric Michael Addition of Ketones to α, β-unsaturated Nitro Compounds

Focusing on Organocatalytic Asymmetric Michael Addition of Ketones to α, β-unsaturated Nitro Compounds

An “(R, R)-1,2-diphenylethylenediamine(DPEN) derivative” organic catalyst was formed as a chiral bifunctional organocatalyst and applied to transβ-nitroalkene compounds under neutral conditions for asymmetric Michael additions of aromatic ketones. High chemical yield and enantioselectivity (ee) are given by the isopropyl-substituted neutral thiourea catalyst (up to 96 percent yield, 98 percent ee). Transformation to highly enantioselective products established the synthetic utility of the present catalytic asymmetric Michael addition. As a muscle relaxant, Baclofen is used, while Phenibut is a sleep inducer. These substances are γ-aminobutyric acid derivatives, an inhibitor of neurotransmission which acts in our bodies on GABA receptors and receptors. Therefore, because of their high applicability in medicine, further investigations into their synthesis are required.

Author(s) Details

Jae Ho Shim
Department of Chemistry, Research Institute for Natural Sciences, Korea University, 145 Anam-ro Seongbuk-gu, Seoul 02841, Korea.

Deok-Chan Ha
Department of Chemistry, Research Institute for Natural Sciences, Korea University, 145 Anam-ro Seongbuk-gu, Seoul 02841, Korea.

Byeong-Seon Kim

Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University, Jinju 52828, South Korea.

Si Hun Nam
Department of Chemistry, Research Institute for Natural Sciences, Korea University, 145 Anam-ro Seongbuk-gu, Seoul 02841, Korea.

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