Bifunctional 2-Aminopyridine-Catalyzed Aza-Friedel–Crafts/Oxa-6π Cascade: Synthesis of 2,2-Disubstituted Chromenes

Organic Letters 2026

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Authors: Azzharuddin Sardar, Shreya Halder, Diljot Singh, Binte Zehra, Tanishkaa Patranabish, Kshatresh Dutta Dubey, Santanu Ghosh
DOI: 10.1021/acs.orglett.6c00685
Cited by: 2
References: 50

Abstract

-dialkyl/aryl chromenes using a bifunctional 2-aminopyridine catalyst. The reaction employs inexpensive phenols and β,β-disubstituted enals and proceeds through an aza-Friedel-Crafts/oxa-6π electrocyclization cascade sequence. This operationally simple and scalable method exhibits a broad substrate scope and enables concise gram-scale syntheses of bioactive chromenes, including precocene I, confluentin, and α-daurichromenic acid, along with the formal synthesis of rhododaurichromanic acid A and (+) α-tocopherol. Detailed hybrid QM/MM MD and physicochemical studies provide mechanistic insight into the catalytic pathway.

Fields of Study & Subjects

Synthesis of Organic Compounds Bioactive natural compounds Synthesis of Indole Derivatives

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
13
Pages
4137–4143
Publication date
24 March 2026
Language
EN