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- Title
Eu(OTf)<sub>3</sub>‐Catalyzed Formal Dipolar [4π+2σ] Cycloaddition of Bicyclo‐[1.1.0]butanes with Nitrones: Access to Polysubstituted 2‐Oxa‐3‐azabicyclo[3.1.1]heptanes.
- Authors
Zhang, Jian; Su, Jia‐Yi; Zheng, Hanliang; Li, Hao; Deng, Wei‐Ping
- Abstract
Herein, we have synthesized multifunctionalized 2‐oxa‐3‐azabicyclo[3.1.1]heptanes, which are considered potential bioisosteres for meta‐substituted arenes, through Eu(OTf)3‐catalyzed formal dipolar [4π+2σ] cycloaddition of bicyclo[1.1.0]butanes with nitrones. This methodology represents the initial instance of fabricating bicyclo[3.1.1]heptanes adorned with multiple heteroatoms. The protocol exhibits both mild reaction conditions and a good tolerance for various functional groups. Computational density functional theory calculations support that the reaction mechanism likely involves a nucleophilic addition of nitrones to bicyclo[1.1.0]butanes, succeeded by an intramolecular cyclization. The synthetic utility of this novel protocol has been demonstrated in the concise synthesis of the analogue of Rupatadine.
- Subjects
ISOXAZOLIDINES; NITRONES; BUTANE; HEPTANE; DENSITY functional theory; RING formation (Chemistry); FUNCTIONAL groups
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 13, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202318476