Structure-Dependent, Switchable Alder-Ene/[2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with α-Ketoesters Enabled by Palladium Catalysis
A structure-dependent, palladium-catalyzed switchable alder-ene/[2π + 2σ] cycloaddition of VBCBs with α-ketoesters has been reported. A variety of cyclobutenes and 2-oxabicyclo[2.1.1]hexanes have been efficiently achieved in good to excellent yields through strain-release-driven alder-ene reactions and [2π + 2σ] cycloadditions, respectively. The potential of this method is illustrated by the scale-up reaction and diverse postsynthetic transformations of the obtained cyclic scaffolds. Additionally, the reaction mechanism and origins of the chemoselectivity have been probed by computational studies.
Authors
- Jun‐An Xiao (ORCID: https://orcid.org/0000-0003-2921-8700)
- Wenjie Liang (ORCID: https://orcid.org/0000-0003-2947-2901)
- Chenxiang Lin (ORCID: https://orcid.org/0000-0001-7041-1946)
- Wei Su (ORCID: https://orcid.org/0000-0002-6017-8543)
- Yang Liu (ORCID: https://orcid.org/0000-0002-1789-6937)
- Hua Yang (ORCID: https://orcid.org/0000-0002-5518-5255)
- Kai Chen (ORCID: https://orcid.org/0000-0003-1012-0383)
- X. Huang (ORCID: https://orcid.org/0000-0002-8654-8469)
- Lan Zheng
- Wei Wang (ORCID: https://orcid.org/0000-0002-8614-7526)
Institutions
- Central South University (CN)
- Nanning Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-04
- DOI
- https://doi.org/10.1021/acs.orglett.4c04251
- Citations
- 11
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.75
Funders
- National Natural Science Foundation of China