Iodine as Polarity-Reversal Catalyst: Synthesis of a Fused Heterocycle with Contiguous Stereocenters
We report an unconventional I<sub>2</sub>-catalyzed cascade reaction for the synthesis of angular triquinane derivatives with a fused heterocycle skeleton, leveraging enaminones and anilines as simple acyclic precursors. The key to success lies in I<sub>2</sub> functioning as a polar-reversal catalyst, which alters the reactivity at the α-position of the enaminone and facilitates the first hexa-functionalization of an enaminone along with the formation of highly congested continuous stereocenters.
Authors
- Ying Song (ORCID: https://orcid.org/0000-0003-4975-6071)
- Hui Zhou (ORCID: https://orcid.org/0000-0001-7474-203X)
- You Zhou (ORCID: https://orcid.org/0009-0007-5054-1875)
- An‐Xin Wu (ORCID: https://orcid.org/0000-0001-7673-210X)
- Yong‐Xing Tang
- Li‐Sheng Wang (ORCID: https://orcid.org/0009-0007-3001-6889)
- Chun‐Yan Wu (ORCID: https://orcid.org/0009-0004-1347-7972)
- Kai‐Lu Zheng
- Zhi‐Cheng Yu
Institutions
- Guangdong Medical College (CN)
- Guangdong Pharmaceutical University (CN)
- Central China Normal University (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-20
- DOI
- https://doi.org/10.1021/acs.orglett.4c03936
- Citations
- 4
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- Ministry of Education of the People's Republic of China
- Higher Education Discipline Innovation Project
- Basic and Applied Basic Research Foundation of Guangdong Province