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Unprecedented Dearomatized Spirocyclopropane in a Sequential Rhodium(III)‐Catalyzed C−H Activation and Rearrangement Reaction
Author(s) -
Wang Xiaoming,
Li Yingzi,
Knecht Tobias,
Daniliuc Constantin G.,
Houk K. N.,
Glorius Frank
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800803
Subject(s) - rhodium , catalysis , chemistry , medicinal chemistry , organic chemistry
An unprecedented dearomatized spirocyclopropane intermediate was discovered in a sequential Cp*Rh III ‐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*Rh III ‐catalyzed dearomatization reaction of N ‐(naphthalen‐1‐yloxy)acetamide with strained olefins was developed, affording a variety of spirocyclopropanes.