高極性反応場を用いるカチオンディールス・アンダー反応の開発と天然物合成への応用
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概要
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Our longstanding interest in the Diels-Alder reactions led us to examine lithium perchlorate in diethyl ether (LPDE) as a medium for effecting [4 + 2] cycloadditions, despite the general view that the rate of the Diels-Alder reaction is essentially independent of solvent polarity. This article describes an effecient, synthetically useful protocol for the construction carbocyclic systems <I>via</I> intramolecular cationic Diels-Alder reactions of <I>in situ</I>-generated heteroatom-stabilized allyl cations in highly polar media. We also present that use of catalytic acid in LPDE to promote intramolecular Diels-Alder reactions of conformationally restricted substrates possessing terminal dienes results in acid catalyzed migration of the diene prior to [4 + 2] cycloaddition.
- 社団法人 有機合成化学協会の論文
- 2000-01-01