Competing Regiodirecting Effects of Ester and Aryl Groups in [3+3] Cyclocondensations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes: Regioselective Synthesis of 3-Hydroxyphthalates and 2-Hydroxyterephthalates
作者： Mohanad Shkoor , Olumide Fatunsin , Abdolmajid Riahi , Mathias Lubbe , Stefanie Reim
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摘要: 3-Hydroxy-5-methylphthalates are prepared by regioselective chelation-controlled cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 4-silyloxy-2-oxo-3-butenoates derived from acetylpyruvates. The employment silylated benzoylpyruvates instead acetylpyruvates results in a regioselectivity change and the formation 6-aryl-2-hydroxyterephthalates. 4-ethoxy-2-oxo-3-butenoates, readily available condensation enol ethers methyl 2-chloro-2-oxoacetate, provides convenient approach to 2-hydroxyterephthalates 3-hydroxyphthalates depending on substitution pattern diene.
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