Affiliation:
1. Key Laboratory of the Ministry of Education for Advanced Catalysis Materials College of Chemistry and Materials Science Zhejiang Normal University 688 Yingbin Road Jinhua 321004 China
2. State Key Laboratory of Bioreactor Engineering Shanghai Key Laboratory of New Drug Design School of Pharmacy East China University of Science and Technology 130 Meilong Road Shanghai 200237 China
Abstract
AbstractHerein, 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.
Funder
National Key Research and Development Program of China
Cited by
11 articles.
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