Concise Synthesis of Chiral Tricyclic Lactams by Tandem Dynamic Kinetic Asymmetric Reductive Amination/Lactamization Using Ammonium Salts

Wang, Jingxin1,2; Shi, Yongjie1; Wang, Fangyuan1; Huang, Fanping1; Bai, Shao-Tao3; Zhao, Yu2; Zhang, Xumu1

2023-05-01

10.1002/anie.202303868

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

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.

Dynamic Kinetic Asymmetric Transformation Enantioselectivity Lactamization Polycyclic Lactams Reductive Amination

SCI ; EI ; IC ; CCR

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China[21991113] ; National Key R&D Program of China["2021YFA1500200","2021YFA0910804"] ; Shenzhen High-Caliber Personnel of SZPT[6023330003K] ; Ministry of Education of Singapore[A-8000055-00-00]

Chemistry

Chemistry, Multidisciplinary

WOS:000983952500001

WILEY-V C H VERLAG GMBH

20231914077379

Amides ; Amines ; Catalysts ; Kinetics ; Salts ; Synthesis (chemical)

Fluid Flow, General:631.1 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804 ; Organic Compounds:804.1 ; Classical Physics; Quantum Theory; Relativity:931

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, 1088 Xueyuan Rd, Shenzhen 518055, Guangdong, Peoples R China
2.Natl Univ Singapore, Dept Chem, 4 Sci Dr 2, Singapore 117544, Singapore
3.Inst Carbon Neutral Technol, Ctr Carbon Neutral Catalysis & Engn, Shenzhen Polytech, 7098 Liuxian Ave, Shenzhen 518055, Peoples R China

Wang, Jingxin,Shi, Yongjie,Wang, Fangyuan,et al. Concise Synthesis of Chiral Tricyclic Lactams by Tandem Dynamic Kinetic Asymmetric Reductive Amination/Lactamization Using Ammonium Salts[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62(25).

Wang, Jingxin.,Shi, Yongjie.,Wang, Fangyuan.,Huang, Fanping.,Bai, Shao-Tao.,...&Zhang, Xumu.(2023).Concise Synthesis of Chiral Tricyclic Lactams by Tandem Dynamic Kinetic Asymmetric Reductive Amination/Lactamization Using Ammonium Salts.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62(25).

Wang, Jingxin,et al."Concise Synthesis of Chiral Tricyclic Lactams by Tandem Dynamic Kinetic Asymmetric Reductive Amination/Lactamization Using Ammonium Salts".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62.25(2023).