Rhodium(III)-Catalyzed Redox-Neutral [4 + 1]-Annulation of Unactivated Alkenes with Sulfoxonium Ylides.

A novel methodology for redox-neutral [4 + 1] annulation of unactivated alkenes with sulfoxonium ylides leads to the synthesis of a diverse library of indanone compounds. The developed annulation reaction was found to be highly versatile due to its compatibility with various unactivated alkenes functionalized with various sensitive functional groups as well as substituted sulfoxonium ylides. Further, multiple transformations such as ring-expansion, reduction, aldol condensation, and Wittig reaction were carried out with indanones. Using this way, highly useful cyclic heterocycles such as indene, dihydroisocoumarin, and 1-indanilidene were prepared in a single step. A possible reaction mechanism was supported by deuterium labeling studies, competitive studies, and kinetic isotopic studies.