Substrate Divergent 4π/6π Electrocyclization of CF3‐Quinolone Heterodendralenes
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A substrate-dependent 4π/6π electrocyclization of in situ generated CF3-heterodendralenes from 4-methyl-3-trifluoroacetyl quinolones is described. Phenyl substitution favors 4π-electrocyclization to give CF3-substituted cyclobuta[c]quinolones bearing a CF3-containing quaternary center, while vinyl substitution promotes 6π-electrocyclization to yield CF3-dihydro-phenanthridones.
Herein, a substrate-divergent 4π/6π electrocyclization of hitherto unknown CF3-heterodendralenes is disclosed, generated in situ from the 4-methyl-3-trifluoroacetyl quinolones. The reaction favors 4π-electrocyclization in the presence of a phenyl substituent, producing cyclobuta[c]quinolones featuring a challenging CF3-all-carbon quaternary stereocenter. Conversely, vinyl substitution promotes 6π-electrocyclization to provide CF3-dihydro-phenanthridones.
