Palladium-Catalyzed Ring Opening of Vinyl Oxetanes Enables Asymmetric Dearomative [6 + 2] Cycloaddition of 3-Nitroindoles to Access Indoline-Fused Oxa-Eight-Membered Rings
We present a catalyst system consisting of a chiral (<i>R</i>)-xyl-BINAP ligand and PdCl<sub>2</sub>, which enables the ring opening of vinyl oxetanes to drive asymmetric dearomatization of 3-nitroindoles for the enantioselective [6 + 2] cycloaddition, leading to the construction of indoline-fused oxa-eight-membered rings in good yields with high to excellent stereoselectivities (up to 96% yield, >95:5 dr, and 98% ee). This work represents the first example of asymmetric dearomatization of electron-deficient nitroindoles triggered by oxa-π-allylpalladium 1,6-dipoles.
Authors
- Junqing Yin (ORCID: https://orcid.org/0000-0002-5240-4256)
- Ming‐Qiang Zhou
- Yang Lei (ORCID: https://orcid.org/0000-0003-0709-4743)
- Jian‐Qiang Zhao (ORCID: https://orcid.org/0000-0002-4444-9630)
- Xinhua Zhang (ORCID: https://orcid.org/0000-0002-4213-5822)
- Zhen‐Hua Wang (ORCID: https://orcid.org/0000-0002-0603-707X)
- Wei‐Cheng Yuan (ORCID: https://orcid.org/0000-0003-4850-8981)
- Yong You (ORCID: https://orcid.org/0000-0002-4689-0235)
- Yan Chen (ORCID: https://orcid.org/0000-0002-9238-4499)
- Jihong Lu
Institutions
- Chinese Academy of Sciences (CN)
- Chengdu Organic Chemicals (China) (CN)
- Jinhua Academy of Agricultural Sciences (CN)
- Innovation Research Center (US)
- Chengdu University (CN)
- Zhejiang Pharmaceutical College (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c03560
- Citations
- 4
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74