Unprecedented Dearomatized Spirocyclopropane in a Sequential Rhodium(III)-Catalyzed C-H Activation and Rearrangement Reaction.
Xiaoming WangYingzi LiTobias KnechtConstantin G DaniliucK N HoukFrank GloriusPublished in: Angewandte Chemie (International ed. in English) (2018)
An unprecedented dearomatized spirocyclopropane intermediate was discovered in a sequential Cp*RhIII -catalyzed C-H activation and Wagner-Meerwein-type rearrangement reaction. How the oxidative O-N bond is cleaved and the role of HOAc were uncovered in this study. Furthermore, a Cp*RhIII -catalyzed dearomatization reaction of N-(naphthalen-1-yloxy)acetamide with strained olefins was developed, affording a variety of spirocyclopropanes.
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