Enantioselective Synthesis of 2-Functionalized Tetrahydroquinolines through Biomimetic Reduction
Zi‐Biao Zhao, Jie Wang, Zhou‐Hao Zhu, Mu‐Wang Chen, Yong‐Gui Zhou
Abstract
Biomimetic asymmetric reduction of 2-functionalized quinolines has been successfully developed with the chiral and regenerable NAD(P)H model CYNAM in the presence of transfer catalyst simple achiral phosphoric acids, providing the chiral 2-functionalized tetrahydroquinolines with up to 99% ee. Using this methodology as a key step, a chiral and potent opioid analgesic containing a 1,2,3,4-tetrahydroquinoline motif was synthesized with high overall yield.
Topics & Concepts
Enantioselective synthesisChemistryCombinatorial chemistryYield (engineering)CatalysisStereochemistryOrganic chemistryMetallurgyMaterials scienceAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisChemical Synthesis and Analysis