Aza-<i>ortho</i>-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines
A strategy for activating azabicyclo[1.1.0]butane (ABB) with <i>in situ</i> generated aza-<i>ortho</i>-quinone methide, promoted by HFIP, is reported. This unified activation, <i>vis-à-vis</i> strain-release-driven N/C3-functionalization, features a new means to prepare functionalized azetidines from ABB. Additionally, the newly installed motif on azetidine nitrogen could be forged into an indoline <i>via</i> Pd-catalyzed hydroamination, leveraging access to medicinally relevant scaffolds.
Authors
- Pujan Sasmal (ORCID: https://orcid.org/0000-0002-6421-8397)
- Jaideep Saha (ORCID: https://orcid.org/0000-0002-1505-5130)
- Bandana Singh (ORCID: https://orcid.org/0000-0002-9599-118X)
- Subhadeep Hazra
- Aaron Taites
Institutions
- National Institute of Pharmaceutical Education and Research - Ahmedabad (IN)
- Centre of Biomedical Research (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c03577
- Citations
- 22
- Primary Topic
- Synthesis of β-Lactam Compounds
- Type
- article
- Field-Weighted Citation Impact
- 5.50
Funders
- Council of Scientific and Industrial Research, India
- Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, India
- Science and Engineering Research Board