Organocatalytic Michael cycloisomerization of bis(enones): the intramolecular Rauhut-Currier reaction.
The utilization of enones as latent enolates enables regioselective enolate formation from chemically robust presursors. In this communication, we report a catalytic Michael cycloisomerization of bis(enones) under Morita-Baylis-Hillman conditions. Upon exposure to 10 mol % tributylphosphine, bis(enone) substrates afford both five- and six-membered ring products. Notably, unsymmetrical bis(enones) possessing sufficient steric or electronic bias yield single isomeric products.
Wang
Long-Cheng
LC
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA.
Luis
Ana Liza
AL
Agapiou
Kyriacos
K
Jang
Hye-Young
HY
Krische
Michael J
MJ
D000475:Alkenes / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*
D000475:Alkenes; D006844:Hydrocarbons, Cyclic; D007659:Ketones