Jiang Qin, Dong Jianyang, Lei Fang, Yu Dejiang, Li Ting, Sun Huaming, Xue Dong
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University Xi'an 710062 China
Chem Sci. 2025 Jun 5. doi: 10.1039/d5sc03141a.
The use of ring strain in bicyclo[1.1.0]butanes (BCBs) to facilitate organic transformations is a powerful strategy in organic synthesis. However, their application to the synthesis of spirocyclic scaffolds has remained challenging. Spirocyclobutanes have attracted considerable interest in medicinal chemistry due to their diverse biological activities and potential clinical applications. In this work, we present a method for scandium-catalyzed spirocyclization of simple BCBs with azomethine imines, creating a new platform for the synthesis of previously inaccessible 6,7-diazaspiro[3.4]octanes. We demonstrate the utility of this approach by performing scaled-up reactions and transforming the products, highlighting its synthetic potential.
利用双环[1.1.0]丁烷（BCB）中的环张力促进有机转化是有机合成中的一种强大策略。然而，将它们应用于螺环骨架的合成仍然具有挑战性。螺环丁烷因其多样的生物活性和潜在的临床应用而在药物化学中引起了相当大的兴趣。在这项工作中，我们提出了一种钪催化简单BCB与甲亚胺亚胺进行螺环化反应的方法，为合成以前难以获得的6,7-二氮杂螺[3.4]辛烷创造了一个新平台。我们通过进行放大反应和转化产物来证明这种方法的实用性，突出了其合成潜力。
