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Synthesis of 9‐Aryl‐9,10‐dihydrophenanthrenes by Domino [3+3] Annulation/Ring‐Opening/Friedel–Crafts Alkylation Reactions of 1,3‐Bis(trimethylsilyloxy)‐1,3‐butadienes with 3‐Aroyl‐5‐aryl‐4,5‐dihydrofurans
Author(s) -
Lau Matthias,
Sher Muhammad,
Villinger Alexander,
Fischer Christine,
Langer Peter
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000451
Subject(s) - annulation , chemistry , friedel–crafts reaction , domino , aryl , alkylation , ring (chemistry) , organic chemistry , medicinal chemistry , catalysis , alkyl
The reaction of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes with 3‐benzoyl‐5‐aryl‐4,5‐dihydrofurans, available by CAN‐mediated reaction of styrenes with benzoylacetones, afforded functionalized 9,10‐dihydrophenanthrenes. These reactions proceed by a novel domino [3+3] cyclization/ring‐opening/Friedel–Crafts alkylation process.