Pd-Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes via [4+3] Cyclization Reaction

Dearomatization of anthranils with vinylcyclopropanes (VCPs) via Pd-catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introd...

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Bibliographic Details
Published inAngewandte Chemie International Edition
Main Authors You, Shuli, Cheng, Qiang, Xie, Jia-Hao, Weng, Yue-Cheng
Format Journal Article
LanguageEnglish
Published Germany 27.02.2019
Subjects
cycloaddition
Pd-catalyzed
dearomatization
asymmetric catalysis
anthranil
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Summary:Dearomatization of anthranils with vinylcyclopropanes (VCPs) via Pd-catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand (L5), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes proceeded with excellent enantioselectivity. Borane plays a key role for the reactivity, likely due to the formation of a borane-anthranil complex which has been confirmed by the NMR experiments.
ISSN:1521-3773