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

页码：3732 / 3742

页数：11

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