Synthesis of Tetrahydroisoquinolines Through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination.

ABSTRACT: Rapid assembly of saturated nitrogen heterocycles-the synthetically more challenging variants of their aromatic relatives-can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.

SUBMITTER: Marcyk PT 

PROVIDER: S-EPMC7423316 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature