Synthesis of vinylcycloheptadienes by the nickel-catalyzed three-component [3 + 2 + 2] cocyclization. Application to the synthesis of polycyclic compounds.
The nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and conjugated enynes proceeded smoothly and divinylcycloheptadienes were isolated in high yields. The three-component cocyclization of ethyl cyclopropylideneacetate, conjugated enynes, and (trimethylsilyl)acetylene also proceeded in a highly selective manner to afford vinylcycloheptadienes, which were reacted with various dienophiles. This study provided a new, short-step synthesis of polycyclic compounds with cycloheptane skeleton.
Komagawa
Shinsuke
S
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.
Takeuchi
Kouhei
K
Sotome
Ikuo
I
Azumaya
Isao
I
Masu
Hyuma
H
Yamasaki
Ryu
R
Saito
Shinichi
S
D000085:Acetates / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D009532:Nickel / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
D000085:Acetates; D000475:Alkenes; D000480:Alkynes; D011083:Polycyclic Compounds; D009532:Nickel