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. 2019 Sep 6;21(17):6741-6744.
doi: 10.1021/acs.orglett.9b02353. Epub 2019 Aug 16.

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

Paul T Marcyk  1 , Silas P Cook  1
Affiliations

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

Paul T Marcyk et al. Org Lett. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1.
Figure 1.
Iron-catalyzed tandem alcohol substitution and hydroamination (TASH) provides a unique disconnection for the synthesis of tetrahydroisoquinolines.
See this image and copyright information in PMC

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