A Dearomatization/Debromination Strategy for the [4+1] Spiroannulation of Bromophenols with α,β‐Unsaturated Imines
Autor: | Cheng Qin, Jiamao Hao, Lu Bai, Xinjun Luan, Jingjing Liu, Yicong Ge |
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Rok vydání: | 2020 |
Předmět: | |
Zdroj: | Angewandte Chemie International Edition. 59:18985-18989 |
ISSN: | 1521-3773 1433-7851 |
Popis: | A novel [4+1] spiroannulation of o- & p-bromophenols with α,β-unsaturated imines has been developed for the direct synthesis of a new family of azaspirocyclic molecules. Notably, several other halophenols (X=Cl, I) were also applicable for this transformation. Moreover, a catalytic asymmetric version of the reaction was realized with 1-bromo-2-naphthols by using a chiral ScIII /Py-Box catalyst. Mechanistic studies revealed that this domino reaction proceeded through electrophile-triggered dearomatization of phenol derivatives at their halogenated positions and followed by halogen-displacement with N-nucleophiles via a radical-based SRN 1 mechanism. |
Databáze: | OpenAIRE |
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