A transition-metal-free multicomponent reaction towards constructing chiral 2H-1,4-benzoxazine scaffolds

Herein, a transition-metal-free multicomponent cascade reaction of readily available α-halogenated ketones, ortho-aminophenols, and aldehydes using a novel dipeptide-based phosphonium salt catalyst was developed for the efficient construction of various 2H-1,4-benzoxazine derivatives with excellent...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2020-01, Vol.22 (21), p.7506-7512
Main Authors: Zhu, Lixiang, Ren, Xiaoyu, Du, Juan, Jia-Hong, Wu, Tan, Jian-Ping, Che, Jixing, Pan, Jianke, Wang, Tianli
Format: Article
Language:English
Subjects:
Aldehydes
Aminophenol
Benzoxazines
Cascade chemical reactions
Catalysts
Crystallography
Green chemistry
Intermediates
Ketones
Scaffolds
Transition metals
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Summary:Herein, a transition-metal-free multicomponent cascade reaction of readily available α-halogenated ketones, ortho-aminophenols, and aldehydes using a novel dipeptide-based phosphonium salt catalyst was developed for the efficient construction of various 2H-1,4-benzoxazine derivatives with excellent functional-group tolerance. The method represents an unprecedented approach for trapping active 1,5-bifunctional intermediates with α-halogenated ketones to access biologically important benzoxazine scaffolds bearing two stereogenic centers with excellent asymmetric induction.
ISSN:1463-9262
1463-9270
DOI:10.1039/d0gc02134b