P(NMe <sub>2</sub> ) <sub>3</sub> -Mediated Umpolung (3 + 2) Annulation of β,γ-Unsaturated α-Keto Carbonyls with <i>p</i> -Quinone Methides: Synthesis of Spirocyclopentenyl <i>p</i> -Dienones
A novel umpolung (3 + 2) annulation reaction between β,γ-unsaturated α-keto carbonyls and <i>p</i>-quinone methides mediated by P(NMe<sub>2</sub>)<sub>3</sub> is described, providing a stereoselective approach to the construction of synthetically interesting, densely functionalized spirocyclopentenyl <i>p</i>-dienones. Notably, vinyl-substituted Kukhtin-Ramirez adducts derived from β,γ-unsaturated α-keto carbonyls are employed, for the first time, as three-carbon synthons in (3 + 2)-annulation reaction.
Authors
- Chun-An Fan
- Yu-Han Yang
- Xiang Zhen (ORCID: https://orcid.org/0000-0002-1510-5548)
- Xian-Tao An
- Mingyuan Ma (ORCID: https://orcid.org/0009-0000-0541-5625)
- Le-Le Meng
- Xi Liu (ORCID: https://orcid.org/0000-0002-6741-4094)
- Yan Deng (ORCID: https://orcid.org/0000-0003-3727-6986)
- Qiang Yang (ORCID: https://orcid.org/0000-0003-2561-4052)
- Xian-He Zhao
- Rui Liu
Institutions
- Ministry of Education of the People's Republic of China (CN)
- Yunnan University (CN)
- State Key Laboratory of Chemical Engineering (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-03-23
- DOI
- https://doi.org/10.1021/acs.orglett.6c00709
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00