Regio- and Diastereoselective [3+2] Annulation of Aliphatic Aldimines with Alkenes by Scandium-Catalyzed β-C(sp3)−H Activation
Xuefeng Cong
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorQingde Zhuo
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorNa Hao
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorZhenbo Mo
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorGu Zhan
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorMasayoshi Nishiura
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorCorresponding Author
Zhaomin Hou
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorXuefeng Cong
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorQingde Zhuo
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorNa Hao
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorZhenbo Mo
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorGu Zhan
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorMasayoshi Nishiura
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorCorresponding Author
Zhaomin Hou
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorAbstract
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.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the Supporting Information of this article.
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