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

Authors
Gao, SY Ko, S Lin, YL Peddinti, RK Liao, CC
Citation
Sy. Gao et al., Inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones with enol ethers and styrene, TETRAHEDRON, 57(2), 2001, pp. 297-308
Citations number
51
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
2
Year of publication
2001
Pages
297 - 308
Database
ISI
SICI code
0040-4020(20010107)57:2<297:IDROMO>2.0.ZU;2-0
Abstract
Regio- and stereoslective inverse-electron-demand Diels-Alder reactions of masked o-benzoquinones (MOBs) la-lh derived from the corresponding 2-methox yphenols 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-ric h dienophile dihydropyran is not a suitable 2 pi -partner for MOBs. Attempt s are made to explain the observed regiochemistry of these Diels-Alder cycl oadditions in terms of frontier molecular orbital theory. (C) 2000 Elsevier Science Ltd. All rights reserved.