Lewis Acid Catalyzed SN2-Type Domino Ring-Opening Cyclization (DROC) of Aziridines with Alkynes: A Synthetic Route to 2,3-Dihydropyrroles
Abstract A simple strategy for the synthesis of a variety of dihydropyrroles in good to excellent yields via a Lewis acid catalyzed, quaternary ammonium salt mediated SN2-type ring opening followed by cyclization of activated aziridines with alkynes in a domino fashion is described. The formation and the observed stereoselectivities of the products via an SN2-/double SN2-type ring-opening pathway are rationalized by mechanistic studies.
Authors
- Manas K. Ghorai (ORCID: https://orcid.org/0000-0002-0472-4757)
- Amit Kumar Sharma (ORCID: https://orcid.org/0000-0001-5255-5452)
- Noimur Rahman (ORCID: https://orcid.org/0000-0002-4062-9247)
- Suraj Kashyap (ORCID: https://orcid.org/0000-0001-5319-7036)
- Aditya Bhattacharyya (ORCID: https://orcid.org/0000-0001-7011-2102)
- Dipti Shukla
- Bharat Singh (ORCID: https://orcid.org/0000-0003-2865-5829)
Institutions
- Indian Institute of Technology Kanpur (IN)
Publication Details
- Journal
- Synthesis
- Published
- 2024-09-13
- DOI
- https://doi.org/10.1055/a-2415-1629
- Citations
- 3
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Indian Institute of Technology Kanpur
- Science and Engineering Research Board