Unprecedented Dearomatized Spirocyclopropane in a Sequential Rhodium(III)‐Catalyzed C−H Activation and Rearrangement Reaction |
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| Authors: | Dr Xiaoming Wang Yingzi Li Tobias Knecht Dr Constantin G Daniliuc Prof K N Houk Prof Frank Glorius |
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| Institution: | 1. Westf?lische Wilhelms-Universit?t Münster, Organisch-Chemisches Institut, Münster, Germany;2. University of California, Department of Chemistry and Biochemistry, Los Angeles, CA, USA |
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| Abstract: | 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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| Keywords: | oxidizing directing groups rhodium catalysis spirocyclopropanes strained olefins |
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