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Concise Synthesis of Chiral Tricyclic Lactams by Tandem Dynamic Kinetic Asymmetric Reductive Amination/Lactamization Using Ammonium Salts |
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| Authors: | Jingxin Wang Dr Yongjie Shi Dr Fangyuan Wang Dr Fanping Huang Prof Dr Shao-Tao Bai Prof Dr Yu Zhao Prof Dr Xumu Zhang |
| Institution: | 1. Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Road, 518055 Shenzhen, Guangdong, P. R. China
Department of Chemistry, National University of Singapore, 4 Science Drive 2, 117544 Singapore, Singapore;2. Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Road, 518055 Shenzhen, Guangdong, P. R. China;3. Center for Carbon-Neutrality Catalysis and Engineering, Institute of Carbon-Neutral Technology, Shenzhen Polytechnic, No. 7098 Liuxian Avenue, Nanshan District, 518055 Shenzhen, P. R. China;4. Department of Chemistry, National University of Singapore, 4 Science Drive 2, 117544 Singapore, Singapore |
| Abstract: | The atom- and step-efficient synthesis of chiral fused tricyclic lactams from readily available ketoesters using cheap ammonium salts as the nitrogen source is reported. This ruthenium-catalyzed system operates through an efficient tandem dynamic kinetic asymmetric reductive amination (ARA)/lactamization and produces chiral fused tricyclic lactams in high yields with excellent diastereo- and enantioselectivity (up to >99 % ee, >20 : 1 dr and 98 % yield). The robust method was also applied to the concise synthesis of key intermediates in the synthesis of rivastigmine analogues and chiral N-heterocyclic carbene catalysts. |
| Keywords: | Dynamic Kinetic Asymmetric Transformation Enantioselectivity Lactamization Polycyclic Lactams Reductive Amination |