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
Rok vydání:	2020
Předmět:	010405 organic chemistry Chemistry General Medicine General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Cascade reaction Molecule Phenol
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0fc3c89fa8d8499c8fa79b6276813c7b https://doi.org/10.1002/anie.202008130 Zobrazit plný text záznamu Plný text