Carbon-carbon bond-forming reaction of cyclic sulfonium ylides stabilized by a carbonyl group.
Rhodium(II)-catalyzed decomposition of diazoketones 1 and 5 bearing a cyclic dithioacetal, in the presence of aldehyde and ClTi(Oi-Pr)(3), afforded both or one of the C=C-bonded products, i.e., ring-enlarged enone 2 and ring-transformed thiophenone 3, that were formed between aldehyde and intermediate bicyclosulfonium ylide. The stereochemistry of the exocyclic C=C bond in the products was exclusively Z. The sulfonium atom that transiently composed the ylide was incorporated into products, but no oxirane was formed.
Sawada
Yuichi
Y
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo, Kyoto 606-8585, Japan.
Oku
Akira
A