Substrate-Controlled Hydrogenation of Flavanones: Selective Synthesis of 2′-Hydroxy-1,3-Diarylpropanes and Flavans |
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Authors: | Dr Martín Soto Paula Pérez-Ramos Prof?Dr Raquel G Soengas Prof?Dr Humberto Rodríguez-Solla |
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Institution: | Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 7, 33006 Oviedo, Spain |
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Abstract: | A new substrate-controlled hydrogenation of flavanones to selectively obtain different hydrogenation products is herein reported. Thus, hydrogenation of flavanones bearing different electron-donating and electron withdrawing substituents (Cl, Br, Me, OMe, OH) provided the corresponding 1,3-diarylpropanes in excellent yields. This procedure offers a straightforward, simple, and cost-effective method for the preparation of glycosylated 2′-hydroxy-1,3-diarylpropanes derived from natural flavanones such as Naringin and Hesperedin. On the contrary, when the hydrogenation was performed over fluorinated flavanones, the corresponding flavans were selectively obtained in excellent yields. |
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Keywords: | diarylpropanes flavans green solvents hydrogenation palladium |
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