3466-80-6Relevant articles and documents
Rapid Synthesis of α-Chiral Piperidines via a Highly Diastereoselective Continuous Flow Protocol
Shan, Chao,Xu, Jinping,Cao, Liming,Liang, Chaoming,Cheng, Ruihua,Yao, Xiantong,Sun, Maolin,Ye, Jinxing
, p. 3205 - 3210 (2022/05/07)
A practical continuous flow protocol has been developed using readily accessible N-(tert-butylsulfinyl)-bromoimine and Grignard reagents, providing various functionalized piperidines (34 examples) in superior results (typically >80% yield and with >90:10 dr) within minutes. The high-performance scale-up is smoothly carried out, and efficient synthesis of the drug precursor further showcases its utility. This flow process offers rapid and scalable access to enantioenriched α-substituted piperidines.
Borane-Catalyzed Reduction of Pyridines via a Hydroboration/Hydrogenation Cascade
Yang, Zhao-Ying,Luo, Heng,Zhang, Ming,Wang, Xiao-Chen
, p. 10824 - 10829 (2021/09/08)
We have developed a method for a B(C6F5)3-catalyzed hydroboration/hydrogenation cascade reduction of pyridines. The method was particularly effective for 2,3-disubstituted pyridines, which generated piperidines in high yields with high cis selectivity. Mechanistic studies indicated that the pyridine substrates and the piperidine products sequentially acted as bases in cooperation with B(C6F5)3to split H2. The broad functional group tolerance of the method allowed its use for the synthesis of some biologically active molecules.
Enantioselective Synthesis of 2-Substituted Pyrrolidines via Intramolecular Reductive Amination
Chang, Mingxin,Guo, Haodong,Huang, Haizhou,Zhang, Tao,Zhao, Wenlei,Zhou, Huan
, p. 2713 - 2719 (2019/06/19)
Catalyzed by the complex generated in situ from iridium and the chiral ferrocene ligand, tert -butyl (4-oxo-4-arylbutyl)carbamate substrates were deprotected and then reductively cyclised to form 2-substituted arylpyrrolidines in a one-pot manner, in which the intramolecular reductive amination was the key step. A range of chiral 2-substituted arylpyrrolidines were synthesised in up to 98percent yield and 92percent ee.