Effective [3+1+1+1] Cycloaddition to Six-Membered Carbocycle Based on DMSO as Dual Carbon Synthon

A [3+1+1+1] cycloaddition was developed among 2-arylpropene, ketone and DMSO in the presence of K2S2O8. 2-arylpropene provides three carbons, ketone offers one carbon, and DMSO as dual carbon donor contributes two carbons to the six-membered carbocycle. It gave the cyclohexene motif and spirocyclohexene skeleton. Four C-C bonds formed in this process. Both propylene and ketone could be well tolerated and give the corresponding cyclohexene or spirocyclohexene motif in useful yields. Based on the controlled experiments, a possible mechanism was proposed.

Automated summary

A new [3+1+1+1] cycloaddition was developed using 2-arylpropene, ketone and DMSO in the presence of K2S2O8, forming cyclohexene motif and spirocyclohexene skeleton with high yields. The reaction resulted in the formation of four C-C bonds.