Inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones with enol ethers and styrene

被引：47

作者：

Gao, SY ^{[1
]}

Ko, S ^{[1
]}

Lin, YL ^{[1
]}

Peddinti, RK ^{[1
]}

Liao, CC ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

TETRAHEDRON | 2001年 / 57卷 / 02期

关键词：

orthoquinone monoketal; 2-methoxyphenols; diacetoxyiodobenzene; bicyclo[2.2.2]octenones; inverse-electron-demand Diels-Alder reaction;

D O I：

10.1016/S0040-4020(00)00937-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regio- and stereoslective inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones (MOBs) la-lh derived from the corresponding 2-methoxyphenols 2a-2h with benzyl vinyl ether, dihydrofuran and styrene to afford the highly functionalized bicyclo[2.2.2]octenone derivatives are described. The MOBs having electron-deficient substituents were found to undergo more facile Diels-Alder cycloadditions with these dienophiles. The electron-rich dienophile dihydropyran is not a suitable 2 pi -partner for MOBs. Attempts are made to explain the observed regiochemistry of these Diels-Alder cycloadditions in terms of frontier molecular orbital theory. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：297 / 308

页数：12

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