Tandem anionic 5-Exo dig cyclization/Claisen rearrangement as an efficient route to fused polycyclic ring systems.
The scope and limitations of a tandem 5-exo dig cyclization/Claisen rearrangement sequence involving appropriately substituted 4-alkyn-1-ols as an efficient "one-pot" route to fused tricyclic ring systems is described. The reaction rates were found to be strongly dependent on the nature of the terminal substitutent of the triple bond. In some cases the entire sequence was found to proceed in good yield at temperatures as low as 115 degrees C.
Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, USA. tvova@conncoll.edu
T V
TV
Ovaska
J B
JB
Roses
D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature
D003508:Cycloheptanes; D011083:Polycyclic Compounds