Development of Cationic Diels-Alder Reaction in Highly Polar Media and Total Syntheses of Natural Products.

DOI Web Site 39 References

Bibliographic Information

Other Title
  • 高極性反応場を用いるカチオンディールス・アルダー反応の開発と天然物合成への応用
  • コウキョクセイ ハンノウバ オ モチイル カチオンディールス アルダー ハンノウ ノ カイハツ ト テンネンブツ ゴウセイ エ ノ オウヨウ

Search this article

Description

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 via intramolecular cationic Diels-Alder reactions of in situ-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.

Journal

References(39)*help

See more

Keywords

Details 詳細情報について

Report a problem

Back to top