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Alternative Coupling Reaction with Unactivated Furan Derivatives

✍ Scribed by Marc-André Giroux; Kimiaka C. Guérard; Marc-André Beaulieu; Cyrille Sabot; Sylvain Canesi

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
134 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Treatment of various dienimides in the presence of a Lewis acid and (trimethylsiloxy)furan leads to the corresponding aniline furan‐2(5__H__)‐ones. The same treatment with furan yields a triaryl product and, surprisingly, a byproduct with a pentacyclo[5.4.0.0.0.0]undecane main core. The formation of this birdcage system containing nine stereogenic centres was produced with complete diastereoselectivity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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