Domino Dearomative Iodocyclization/Intramolecular Diels–Alder Reaction for Rapid Construction of Polycyclic Scaffolds
We report a domino dearomative iodocyclization/intramolecular Diels-Alder (IMDA) reaction sequence that converts planar aromatic precursors into complex three-dimensional polycyclic scaffolds. The initial dearomative iodocyclization affords spirodienones, which can serve as dienophiles for a subsequent IMDA reaction with an internal diene. This protocol simultaneously creates three C-C bonds, three rings, and five stereocenters in a single step with excellent diastereoselectivity. This protocol is applicable to a broad range of substituents and ring systems for achieving iodinated, sp<sup>3</sup>-rich polycycles.
Authors
- Takayuki Yakura (ORCID: https://orcid.org/0000-0002-7249-6151)
- Takashi Okitsu (ORCID: https://orcid.org/0000-0001-5836-4470)
- Hikaru Saito (ORCID: https://orcid.org/0000-0001-9578-1433)
- Kiyoshi Tsuge (ORCID: https://orcid.org/0000-0003-1536-3261)
Institutions
- University of Toyama (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-12-12
- DOI
- https://doi.org/10.1021/acs.joc.5c02516
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00