Highly efficient trapping of the Nazarov intermediate with substituted arenes.
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.
Browder
C C
CC
Department of Chemistry, University of Utah, 315 South 1400 East, Rm 2020, Salt Lake City, UT 84112-0850, USA.
Marmsäter
F P
FP
West
F G
FG
D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; D006844:Hydrocarbons, Cyclic; C025096:titanium tetrachloride; D014025:Titanium