Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control
A regioselective intramolecular nitrone-alkene cycloaddition for synthesizing oxazabicyclo ring-fused indoles is reported. Computational studies guided the development of optimal conditions using In(OTf)<sub>3</sub> as a Lewis acidic reagent. This method demonstrates a broad substrate scope, forming seven- and eight-membered carbocycles with various substituents, and provides a versatile route to complex nitrogen-containing scaffolds with potential applications in medicinal chemistry and the total synthesis of biologically active compounds.
Authors
- Tetsuhiro Nemoto (ORCID: https://orcid.org/0000-0001-8858-161X)
- Tomohiro Yazawa
- Tanawat Phumjan
- Shinji Harada (ORCID: https://orcid.org/0000-0003-4042-9744)
Institutions
- Chiba University (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-05
- DOI
- https://doi.org/10.1021/acs.orglett.5c00125
- Citations
- 6
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- Fugaku Trust for Medicinal Research
- Japan Society for the Promotion of Science
- Institute for Global Prominent Research, Chiba University