articleAngewandte Chemie International EditionJan 30, 2024Closed access

Eu(OTf) 3 ‐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

JZJian ZhangJSJia‐Yi SuHZHanliang ZhengHLHao LiWDWei‐Ping Deng

Zhejiang Normal University · East China University of Science and Technology

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Abstract

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…

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Topics & keywords

Topics
Keywords
  • Bicyclic molecule
  • Cycloaddition
  • Chemistry
  • Intramolecular force
  • Nucleophile
  • Catalysis
  • Heteroatom
  • Medicinal chemistry
UN Sustainable Development Goals
  • Clean water and sanitation
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