Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 23, Pages 3871-3874Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900542
Keywords
Oxygen heterocycles; Michael addition; Aromaticity; Cross-coupling; Sulfonamides
Categories
Funding
- American Chemical Society (ACS)
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Provincial Government of Quebec (FQRNT)
- Boehringer Ingelheim (Canada) Ltd.
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Treatment of various dienimides in the presence of a Lewis acid and (trimethylsiloxy)furan leads to the corresponding aniline furan-2(5H)-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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