Asymmetric Synthesis of Fused-Ring Tetrahydroisoquinolines and Tetrahydro-β-carbolines from 2-Arylethylamines via a Chemoenzymatic Approach

While chiral fused-ring tetrahydroisoquinoline (THIQ) and tetrahydro-beta-carboline (TH beta C) scaffolds have attracted considerable interest due to their wide spectrum of biological activities, the synthesis of optically pure chiral fused-ring THIQs and TH beta Cs remains a challenging task. Herein, a group of active imine reductases were identified to convert the imine precursors into the corresponding enantiocomplementary fused-ring THIQs and TH beta Cs with high enantioselectivity and conversion, establishing an efficient and green chemoenzymatic approach to fused-ring alkaloids from 2-arylethylamines.

Automated summary

In this study, an efficient and environmentally friendly enzymatic approach was developed to synthesize optically pure chiral fused-ring THIQs and TH β Cs with high enantioselectivity and conversion.