1240314-06-0Relevant articles and documents
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
Shkoor, Mohanad,Fatunsin, Olumide,Riahi, Abdolmajid,Lubbe, Mathias,Reim, Stefanie,Sher, Muhammad,Villinger, Alexander,Fischer, Christine,Langer, Peter
, p. 3732 - 3742 (2010)
3-Hydroxy-5-methylphthalates are prepared by regioselective chelation-controlled cyclization of 1,3-bis(silyloxy)-1,3butadienes with 4-silyloxy-2-oxo-3-butenoates derived, from acetylpyruvates. The employment of silylated benzoylpyruvates instead of acetylpyruvates results in a regioselectivity change and the formation, of 6-aryl-2-hyd:roxyterephthalates. The cyclization of l,3-bis(silyloxy)-l,3-butadienes with 4ethoxy-2-oxo-3- butenoates, readily available by condensation of enol ethers with methyl 2-chloro-2-oxoacetate, provides a convenient approach to 2-hydroxyterephthalates and 3-hydroxyphthalates depending on the substitution pattern of the diene.
