Lewis Acid Promoted Tandem Intermolecular Diels−Alder/Intramolecular Allylation Reactions of Silyl-Substituted 1,3-Butadienes Leading to Multisubstituted 7-Norbornenones and Related Polycyclic Compounds

Lewis Acid Promoted Tandem Intermolecular Diels−Alder/Intramolecular Allylation Reactions of Silyl-Substituted 1,3-Butadienes Leading to Multisubstituted 7-Norbornenones and Related Polycyclic Compounds

7-Norbornenones of exo,exo-disubstituted patterns were formed highly selectively in good yields from Lewis acid-promoted tandem intermolecular Diels−Alder/intramolecular allylation reactions. The intermolecular Diels−Alder reaction between 1,4-bis(trimethylsilyl)-1,3-butadienes or 1-trimethylsilyl-1...

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Veröffentlicht in:Organic letters 2007-12, Vol.9 (26), p.5433-5436
Hauptverfasser: Li, Dongzhen, Liu, Guangzhen, Hu, Qiaoshu, Wang, Chao, Xi, Zhenfeng
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Sprache:eng
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Boron Compounds - chemistry
Butadienes - chemistry
Models, Molecular
Polycyclic Compounds - chemistry
X-Ray Diffraction
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container_end_page 5436
container_issue 26
container_start_page 5433
container_title Organic letters
container_volume 9
creator Li, Dongzhen
Liu, Guangzhen
Hu, Qiaoshu
Wang, Chao
Xi, Zhenfeng
description 7-Norbornenones of exo,exo-disubstituted patterns were formed highly selectively in good yields from Lewis acid-promoted tandem intermolecular Diels−Alder/intramolecular allylation reactions. The intermolecular Diels−Alder reaction between 1,4-bis(trimethylsilyl)-1,3-butadienes or 1-trimethylsilyl-1,3-butadienes with maleic anhydride in the presence of newly sublimed AlCl3 afforded their corresponding cycloaddition adducts, which underwent AlCl3-mediated intramolecular allylation of the carbonyl group by the in situ generated allylsilane moiety affording 7-norbornenones of exo,exo-disubstituted patterns.
doi_str_mv 10.1021/ol702379s
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subjects Boron Compounds - chemistry
Butadienes - chemistry
Models, Molecular
Polycyclic Compounds - chemistry
X-Ray Diffraction
title Lewis Acid Promoted Tandem Intermolecular Diels−Alder/Intramolecular Allylation Reactions of Silyl-Substituted 1,3-Butadienes Leading to Multisubstituted 7-Norbornenones and Related Polycyclic Compounds
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