Development of a Cationic Cascade Trailing into Piancatelli Rearrangement En Route to Skeletally Diverse Polycyclic Frameworks
The aza-Piancatelli rearrangement represents a powerful strategy for accessing complex cyclopentenones, starting from furan carbinols. We demonstrate herein the use of a noncanonical furan building block and show that this reaction can be effectively combined with an azaoxyallyl cation-centered process. This integration leads to elusive polycyclic scaffolds bearing multiple contiguous stereocenters. The H-bonding clusters of HFIP serve as the sole promoter, highlighting a rapid, diversity-oriented synthesis of cyclopentanoid architectures.
Authors
- Chenna Jagadeesh
- Abhijit Nandy (ORCID: https://orcid.org/0009-0001-0719-2813)
- Shibdas Banerjee (ORCID: https://orcid.org/0000-0002-3424-8157)
- Dinabandhu Das (ORCID: https://orcid.org/0000-0003-0143-7821)
- Jaideep Saha (ORCID: https://orcid.org/0000-0002-1505-5130)
- Manveer Patel (ORCID: https://orcid.org/0009-0007-0375-9433)
Institutions
- Indian Institute of Science Education and Research Kolkata (IN)
- Jawaharlal Nehru University (IN)
- Indian Institute of Science Education and Research Mohali (IN)
- Indian Institute of Science Education and Research, Bhopal (IN)
- National Institute of Pharmaceutical Education and Research - Ahmedabad (IN)
- Indian Institute of Science Education and Research Berhampur (IN)
- Indian Institute of Science Education and Research, Tirupati (IN)
- Centre of Biomedical Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-12
- DOI
- https://doi.org/10.1021/acs.orglett.5c03061
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00