Hydrogen-Bonding Assisted Catalytic 1,2-Addition Reaction of Trifluoropyruvate with 2,4-Dihydrocylopenta[<i>b</i>]indoles
CF<sub>3</sub>-substituted tertiary alcohols are valuable as biologically active compounds, but the synthesis of the corresponding cyclopentadiene derivatives remains challenging. The DABCO-catalyzed 1,2-addition reaction of trifluoropyruvates with 2,4-dihydrocyclopenta[<i>b</i>]indoles has been developed, affording CF<sub>3</sub>-substituted tertiary alcohols in up to 90% yield and with up to >99:1 dr. The catalytic reaction is facilitated by hydrogen bonding (N-H···N) between the cyclic tertiary amine and the indole moiety. Additionally, Et<sub>3</sub>N (1.0 equiv) can promote the retro-1,2-addition reaction of the CF<sub>3</sub>-subsituted tertiary alcohols, yielding dihydrocyclopenta[<i>b</i>]indole <b>1</b> in up to 72% yield.
Authors
- Daoshan Yang (ORCID: https://orcid.org/0000-0002-3047-5416)
- K. Sandy Pang (ORCID: https://orcid.org/0000-0002-0683-2129)
- Ran Song
- Man Wang (ORCID: https://orcid.org/0000-0003-2675-8701)
- Xin Li (ORCID: https://orcid.org/0000-0001-9050-6504)
- Jian Lv (ORCID: https://orcid.org/0000-0001-7641-5411)
Institutions
- Qingdao University of Science and Technology (CN)
- Nanjing Forestry University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-15
- DOI
- https://doi.org/10.1021/acs.joc.5c00418
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- Natural Science Foundation of Shandong Province
- Qingdao University of Science and Technology