Lewis Acid-Catalyzed Divergent (4+3)/(4+2) Annulations of <i>o</i> -Quinone Methides with Bicyclo[1.1.0]butanes Lead to sp <sup>3</sup> -Rich Oxabicyclic Frameworks
Benzannulation strategies that attach a planar arene ring to cyclic, saturated, three-dimensional bridged motifs are becoming valuable for drug discovery. Herein, a Lewis acid-catalyzed [4+3] annulation of <i>in situ</i>-generated <i>o</i>-QMs with bicyclo[1.1.0]butanes is developed. Reaction modulation further leveraged a telescoped [4+2] annulation of <i>o</i>-QMs with the <i>in situ</i>-formed cyclobutanes, leading to diversified sp<sup>3</sup>-rich oxabicyclic architectures. Overall, this study expands the scope for a new bioisosteric space for medicinal chemistry.
Authors
- Soumik Mondal
- Jaideep Saha (ORCID: https://orcid.org/0000-0002-1505-5130)
- Subhadeep Hazra
- Manveer Patel (ORCID: https://orcid.org/0009-0007-0375-9433)
- Saumen Hajra
Institutions
- Centre of Biomedical Research (IN)
- University of Kalyani (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-01-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c04897
- Citations
- 1
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 22.95