Work

Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines

Year: 2024

Type: article

Abstract: The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because of their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes a Lewis acid (Sc(OTf) 3 )‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond of bicyclobutanes and the C−N bond of diaziridines to produce multifunctionalized and medicinally interesting azabicyclo[3.1.1]heptane derivatives. The reaction proceeds well with different bicyclobutanes and a broad range of aryl‐ as well as alkenyl‐, but also alkyl‐substituted diaziridines (up to 98 % yield). Conducting a scale‐up experiment and exploring the synthetic transformations of the cycloadducts emphasized the practical application of the synthesis. Furthermore, a zinc‐based chiral Lewis acid catalytic system was developed for the enantioselective version of this reaction (up to 96 % ee ).

Source: Angewandte Chemie

DOI: 10.1002/ange.202416741

Authors: Heng‐Xian He, Feng Wu, Xu Zhang, Jian‐Jun Feng

Institutions: Hunan University, Yangzhou University

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Fudan University, Fundamental Research Funds for the Central Universities

Award: G1447870626