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

被引：7
|
作者：
Shkoor, Mohanad [1 ]
Fatunsin, Olumide [1 ]
Riahi, Abdolmajid [1 ,2 ]
Lubbe, Mathias [1 ]
Reim, Stefanie [1 ]
Sher, Muhammad [1 ,2 ,3 ]
Villinger, Alexander [1 ]
Fischer, Christine [2 ]
Langer, Peter [1 ,2 ]
机构：
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
[3] Allama Iqbal Open Univ, Dept Chem, Islamabad, Pakistan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 19期
关键词：
Arenes; Cyclization; Regioselectivity; Silicon; Enols; 1,3-BIS(SILYL ENOL ETHERS); ONE-POT SYNTHESIS; REARRANGEMENT; CYCLIZATIONS; DERIVATIVES; KETONES; ELECTROPHILES; CHELATION; CHEMISTRY; ACYLATION;
D O I：
10.1002/ejoc.200901373
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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 of silylated benzoylpyruvates instead of acetylpyruvates results hi a regioselectivity change and the formation of 6-aryl-2-hydroxyterephthalates. The cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 4-ethoxy-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.
引用
收藏
页码：3732 / 3742
页数：11
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