Stereoselective Synthesis of 3-Substituted Tetrahydropyrazinoisoquinolines via Intramolecular Cyclization of Enantiomerically Enriched Dihydro-2H-pyrazines

The preparation of 3-substituted tetrahydropyrazinoisoquinolines using the tributyltin hydride mediated intramolecular radical cyclization of suitably protected 2-substituted 3,4-dihydropyrazines is reported. The compounds are obtained as single enantiomers, as the relative configuration of the new generated stereogenic center is driven by the stereochemistry of the 2-substituted carbon in the starting materials, which is in turn derived from naturally occurring amino acids.