DBU-Promoted Cascade Synthesis of Dihydrocoumarins from p -Quinone Methides and o -Hydroxy Aldimines

The Journal of Organic Chemistry 2026

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Authors: Yingpeng Su, Qinqin Ling, Caixia Yang, Zhengang Han, Haiyang He, Shufang Zhang, Jinjin Chang, Xinyu Zhao, Congde Huo, Xiaolei Wang
DOI: 10.1021/acs.joc.5c02600
Cited by: 3
References: 78

Abstract

A facile synthesis of dihydrocoumarin derivatives has been successfully accessed with ortho -hydroxyphenyl-substituted para -quinone methides ( p -QMs) and ortho -hydroxy aromatic aldimines. The reaction proceeds through a Michael addition followed by an intramolecular phenolysis sequence. This cascade strategy provides structurally diverse 4-aryl-3,4-dihydrocoumarins in good to excellent yields with excellent diastereoselectivity. Moreover, this versatile method exhibits significant promise for the synthesis of natural products and biologically relevant compounds that possess a substituted coumarin skeleton.

Fields of Study & Subjects

Synthesis of Indole Derivatives Multicomponent Synthesis of Heterocycles Catalytic Alkyne Reactions

Publication details

Journal / source
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Volume
91
Issue
6
Pages
2404–2415
Publication date
2 February 2026
Language
EN