Triethylamine-Catalyzed Cyclization of Unsaturated Hydroperoxides in the Presence of Triethylammonium Hydrochloride: A Synthesis of 1,2-Dioxanes
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<sub>3</sub>Cl) and catalytic Et<sub>3</sub>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.
Authors
- K. A. Woerpel (ORCID: https://orcid.org/0000-0002-8515-0301)
- John P. Stasiak
Institutions
- New York University (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-26
- DOI
- https://doi.org/10.1021/acs.orglett.4c04629
- Citations
- 2
- Primary Topic
- Chemical Synthesis and Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- NIH Office of the Director
- National Institute of General Medical Sciences
- Division of Chemistry