Polar and e-Radical Strain-Release Strategies for Accessing Functionalized 2-Oxabicyclo[2.1.1]hexan-3-ones from Bicyclo[1.1.0]butanes
Abstract 2-Oxabicyclo[2.1.1]hexanes (OBHs) have emerged as valuable saturated aromatic replacements, whereas their lactone analogues, 2-oxabicyclo[2.1.1]hexan-3-ones (OBHOs) remain underexplored, because of limited synthetic access. Herein, we report complementary polar and electrochemical strain-release strategies for the modular synthesis of 1,4-difunctionalized OBHOs from bicyclo[1.1.0]butane carboxylic acids. The two activation modes provide complementary perspectives toward the chemical space expansion of this underexplored scaffold.
Authors
- Giulio Bertuzzi (ORCID: https://orcid.org/0000-0003-4090-8462)
- Andrea Brunetti (ORCID: https://orcid.org/0009-0002-6915-1918)
- Renzo Luisi (ORCID: https://orcid.org/0000-0002-9882-7908)
- Marco Colella (ORCID: https://orcid.org/0000-0001-7673-5335)
- Marco Bandini (ORCID: https://orcid.org/0000-0001-9586-3295)
- Elena Graziano (ORCID: https://orcid.org/0000-0002-0956-0560)
- Luisa Pisano (ORCID: https://orcid.org/0000-0003-2782-5400)
- Leonardo Degennaro (ORCID: https://orcid.org/0000-0002-2187-9419)
- Giulia Monda
- Samuele Usai
Institutions
- University of Sassari (IT)
- University of Bologna (IT)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-09-26
- DOI
- https://doi.org/10.1021/acs.orglett.6c03497
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00