72475-12-8Relevant articles and documents
Regio- and Diastereoselective [3+2] Annulation of Aliphatic Aldimines with Alkenes by Scandium-Catalyzed β-C(sp3)?H Activation
Cong, Xuefeng,Zhuo, Qingde,Hao, Na,Mo, Zhenbo,Zhan, Gu,Nishiura, Masayoshi,Hou, Zhaomin
supporting information, (2021/12/30)
Here we report for the first time the regio- and diastereoselective [3+2] annulation of a wide range of aliphatic aldimines with alkenes via the activation of an unactivated β-C(sp3)?H bond by half-sandwich scandium catalysts. This protocol offers a straightforward and atom-efficient route for the synthesis of a new family of multi-substituted aminocyclopentane derivatives from easily accessible aliphatic aldimines and alkenes. The annulation of aldimines with styrenes exclusively afforded the 5-aryl-trans-substituted 1-aminocyclopentane derivatives with excellent diastereoselectivity through the 2,1-insertion of a styrene unit. The annulation of aldimines with aliphatic alkenes selectively gave the 4-alkyl-trans-substituted 1-aminocyclopentane products in a 1,2-insertion fashion. A catalytic amount of an appropriate amine such as adamantylamine (AdNH2) or dibenzylamine (Bn2NH) showed significant effects on the catalyst activity and stereoselectivity.