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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)