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

Full Text: HTML

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 ...