Alternative Coupling Reaction with Unactivated Furan Derivatives | Zendy

Giroux MarcAndré | Zendy; Guérard Kimiaka C. | Zendy; Beaulieu MarcAndré | Zendy; Sabot Cyrille | Zendy; Canesi Sylvain | Zendy

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Alternative Coupling Reaction with Unactivated Furan Derivatives

Author(s) -

Giroux MarcAndré,

Guérard Kimiaka C.,

Beaulieu MarcAndré,

Sabot Cyrille,

Canesi Sylvain

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200900542

Subject(s) - furan , chemistry , aniline , stereocenter , undecane , lewis acids and bases , organic chemistry , stereochemistry , medicinal chemistry , enantioselective synthesis , catalysis

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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