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Issue 21, 2020
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A transition-metal-free multicomponent reaction towards constructing chiral 2H-1,4-benzoxazine scaffolds

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Abstract

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.

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

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Article information


Submitted
23 Jun 2020
Accepted
11 Sep 2020
First published
11 Sep 2020

Green Chem., 2020,22, 7506-7512
Article type
Paper

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

L. Zhu, X. Ren, J. Du, J. Wu, J. Tan, J. Che, J. Pan and T. Wang, Green Chem., 2020, 22, 7506
DOI: 10.1039/D0GC02134B

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