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Triethylamine-Catalyzed Cyclization of Unsaturated Hydroperoxides in the Presence of Triethylammonium Hydrochloride: A Synthesis of 1,2-Dioxanes

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Unsaturated hydroperoxides were synthesized from dienes using a regioselective cobalt-catalyzed hydroperoxidation reaction. Subsequent intramolecular oxa-Michael reactions in the presence of triethylammonium hydrochloride (HNEt 3 Cl) and catalytic Et 3 N formed 1,2-dioxanes, in several cases with high diastereoselectivity. These 1,2-dioxanes could be transformed to their respective carboxylic acids, without affecting the integrity of the peroxide linkage, to form compounds with structures that resemble biologically active natural products.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c04629

Authors: John P. Stasiak, K. A. Woerpel

Institution: New York University

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Institutes of Health, NIH Office of the Director, National Institute of General Medical Sciences, Division of Chemistry