Synthesis of Functionalized 3‐Azabicyclo[3.2.0]Heptanes via Visible‐Light Energy‐Transfer Catalysis
Abstract Functionalized cyclobutanes are three‐dimensional scaffolds widely found in natural products and bioactive molecules. Herein, we report a visible‐light‐induced intermolecular [2+2] cycloaddition reaction of a diverse array of alkenes with N ‐substituted maleimides to access functionalized azabicyclo[3.2.0]heptanes. The reaction showed broad substrate scope with good chemo‐, regio‐ and diastereoselectivity under mild conditions. The robustness of this photo‐mediated [2+2] cycloaddition was demonstrated by carrying out a reaction on a 100 g scale (58 % yield). The prepared functionalized azabicyclo[3.2.0]heptanes are synthetic scaffolds for drug discovery.
Authors
- Anuradha Gupta (ORCID: https://orcid.org/0000-0002-4211-1441)
- Mysore S. Pavan (ORCID: https://orcid.org/0000-0001-9751-7345)
- Arvind Mathur (ORCID: https://orcid.org/0000-0003-3146-8485)
- Mahammed Kaspady (ORCID: https://orcid.org/0000-0003-2238-2006)
- Muthalagu Vetrichelvan (ORCID: https://orcid.org/0000-0001-7201-4143)
- James Kempson (ORCID: https://orcid.org/0000-0002-9540-3886)
- Martins S. Oderinde (ORCID: https://orcid.org/0000-0002-6858-321X)
- Gopikumar Indasi
- Manivel Pitchai (ORCID: https://orcid.org/0000-0003-0749-0930)
- Madhavan Kannan
- Arunkumar Akunuri
Institutions
- Bristol-Myers Squibb (United States) (US)
- Biocon (India) (IN)
- Syngene International (India) (IN)
Publication Details
- Journal
- ChemistrySelect
- Published
- 2024-10-28
- DOI
- https://doi.org/10.1002/slct.202404151
- Citations
- 1
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.25