Wen Jialin, Tan Renchang, Liu Shaodong, Zhao Qingyang, Zhang Xumu
Department of Chemistry & Chemical Biology , Rutgers, The State University of New Jersey , 610 Taylor Road , Piscataway , New Jersey 08854 , USA . Email:
College of Chemistry & Materials Science , Northwest University , 1 Xuefu Road , Xi'an , 710127 , China . Email:
Chem Sci. 2016 May 1;7(5):3047-3051. doi: 10.1039/c5sc04712a. Epub 2016 Jan 26.
Rhodium catalyzed asymmetric hydrogenation of both isoquinolines and quinolines provides a new method to synthesize chiral tetrahydroisoquinolines and tetrahydroquinolines. By introducing strong Brønsted acid HCl, anion binding between the substrate and the ligand was established to achieve high reactivity and high enantioselectivity (up to 99% conversion and 99% ee). An NMR study suggests an anion binding between the catalyst and the substrate. Deuterium labeling experiments reveal a plausible reaction pathway.
铑催化异喹啉和喹啉的不对称氢化反应为合成手性四氢异喹啉和四氢喹啉提供了一种新方法。通过引入强布朗斯特酸HCl，在底物和配体之间建立了阴离子结合，以实现高反应活性和高对映选择性（转化率高达99%，对映体过量值高达99%）。核磁共振研究表明催化剂与底物之间存在阴离子结合。氘标记实验揭示了一条合理的反应途径。
