Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction.
A catalytic domino reaction producing substituted 2-alkylidenecyclohexanone from 3-oxymethyl-2-siloxy-1,3-butadienes, which can be prepared from Baylis-Hillman adducts, and α,β-unsaturated ketones is described. The process involves two mechanistically distinct reactions, (4+2) cycloaddition and elimination. Both of these reactions are catalyzed by Tf(2)NH.
Takasu
Kiyosei
K
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8571, Japan. kay-t@pharm.kyoto-u.ac.jp
Tanaka
Toru
T
Azuma
Takumi
T
Takemoto
Yoshiji
Y
D002070:Butadienes / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry
D002070:Butadienes; D003512:Cyclohexanones; D007659:Ketones; D008698:Mesylates; C538740:triflic imide; C031763:1,3-butadiene