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Highly efficient trapping of the Nazarov intermediate with substituted arenes
C C Browder1, F P Marmsäter, F G West
1Department of Chemistry, University of Utah, 315 South 1400 East, Rm 2020, Salt Lake City, UT 84112-0850, USA.
Organic Letters
|September 14, 2001
Abstract:
1,4-Dien-3-ones bearing pendant arylethyl side chains were readily prepared from substituted dihydrocinnamaldehydes. When treated with TiCl(4) at low temperature, these compounds underwent domino cyclization to give benzohydrindenones in near-quantitative yield and with complete diastereoselectivity. Reaction: see text.