Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: merging organic and transition metal catalysis.
Upon exposure of mono-enone mono-allylic carbonates to tributylphosphine and 1 mol % Pd(Ph3P)4, efficient conversion to the corresponding cycloallylated products is achieved. This transformation combines the nucleophilic features of the Morita-Baylis-Hillman reaction with the electrophilic features of the Trost-Tsuji reaction.
Jellerichs
Bradley G
BG
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA.
Kong
Jong-Rock
JR
Krische
Michael J
MJ
D000475:Alkenes / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry
D000475:Alkenes; D000498:Allyl Compounds; D006844:Hydrocarbons, Cyclic; D007659:Ketones; D009942:Organometallic Compounds; D010720:Phosphines; C043255:tri-n-butylphosphine; D010165:Palladium