Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization electrophilic aromatic substitution
CC Browder, FP Marmsäter…
Index: Browder, Cindy C.; Marmsaeter, Fredrik P.; West Canadian Journal of Chemistry, 2004 , vol. 82, # 2 p. 375 - 385
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Citation Number: 26
Abstract
1, 4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity. Key words: domino process, electrophilic aromatic substitution, Lewis ...
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