Zikun Lin, Bingni Wang, Xiaoying Nong, Shixi Wu
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China
Lot of natural products, pharmaceuticals and functional materials with chiral amines do many useful job, and this group also a valuable constituents of versatile building blocks and important chiral catalysts as well as chiral auxiliaries in organic synthesis. Therefore, to develop efficient methods for the synthesis of structurally diverse chiral amines and chiral amine scaffolds has great importance and huge application vaule. symmetric catalysis is the most efficient method to synthesize chiral organic molecules. Cooperatively catalyzed by transition metal and small organic molecules can be used to simultaneously or continuously activates the bonds and rebuild, it can help some reaction which can not happen with only one catalyst to move on. This article reviews some cases of chiral nitrogen formation through metal catalysis, organic small molecule catalysis and their synergistic catalysis, and briefly discusses the challenges and future development directions in this area.
Organic small molecule. Metal catalysis. Construction of chiral C-N bond. Asymmetric catalysis
Zikun Lin, Bingni Wang, Xiaoying Nong, Shixi Wu. Advances in Asymmetric N Construction of Metal and Organic Small Molecules. Academic Journal of Materials & Chemistry (2022) Vol. 3, Issue 1: 58-61. https://doi.org/10.25236/AJMC.2022.030110.
 X. Xin. USTC makes progress in chiral amine synthesis [J]. New Chemical Materials, 2021, 49 (05): 68.
 Y. Li, M. Xu. Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines [J]. Acta Chimica Sinica, 2021, 79(11): 1345-1359.
 H. Yang, S. You. Asymmetric Organocatalysis: An Ingenious Tool for Building Chiral Molecules [J]. Science, 2022, 74(01): 35-39+4.
 J. A. Ellman. Applications of tert-butanesulfinamide in the asymmetric synthesis of amines [J]. Pure and Applied Chemistry, 2003, 75(1): 39–46.
 M. T. Robak, M. A. Herbage, J. A. Ellman. Synthesis and applications of tert-butanesulfinamide [J]. Chemical Reviews, 2010, 110(6): 3600–3740.
 H. Xu, S. Chowdhury, J. A Ellman. Asymmetric synthesis of amines using tert-butanesulfinamide [J]. Nature Protocols, 2013, 8(11): 2271–2280.
 M. Kazak, M. Priede, K. Shubin, et al. Stereodivergent synthesis of pseudotabersonine alkaloids [J]. Organic Letters, 2017, 19(19): 5356–5359.
 Y. Zhu, H. Li, K. Lin, et al. A novel and efficient asymmetric synthesis of anti-HIV drug maraviroc [J]. Synthetic Communications, 2019, 49(13): 1721–1728.
 B. Liu, M. Xu. Transition metal-catalyzed asymmetric carbene insertion for synthesis of chiral amines [J]. Chinese Science Bulletin, 2021, 66: 3251–3260.
 Y. Wang, Q. Wang, J. Zhu. Organocatalytic Nucleophilic Addition of Hydrazones to Imines: Synthesis of Enantioenriched Vicinal Diamines [J]. Angew. Chem. Int. Ed. 2017, 56: 5612–5615.
 F. Jiang, D. Zhao, X. Yang, et al. Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines [J]. ACS Catal. 2017, 7, 10: 6984–6989.
 L. Gong. Asymmetric Organocatalysis Combined with Metal Catalysis: A Promising and Emerging Field [J]. Acta Chimica Sinica, 2018, 76(11): 817-818.
 J. Jiang, H. Xu, J. Xi, et al. Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines [J]. J. Am. Chem. Soc. 2011, 133, 22: 8428–8431.
 L. Jiang, D. Zhang, Z. Wang, W. Hu. Highly Enantioselective Three-Component Reactions of tert-Butyl Diazoacetate with Arylamines and Imines: An Efficient Synthesis of α, β-Bis (arylamino) Acid Derivatives [J]. Synthesis, 2013; 45(4): 452-458.
 L. Ren, X. Lian, L. Gong. Brønsted Acid/Rhodium (II) Cooperative Catalytic Asymmetric Three-Component Aldol-Type Reaction for the Synthesis of 3-Amino Oxindoles [J]. Chem. Eur. J. 2013, 19(10): 3315-3318.