Substrate‐Controlled Hydrogenation of Flavanones: Selective Synthesis of 2′‐Hydroxy‐1,3‐Diarylpropanes and Flavans.

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. [ABSTRACT FROM AUTHOR]