Catalytic, selective, and stereocontrolled construction of C4 quaternary and homobenzylic dihydroisoquinolones by sp³ C-H benzylation.

ABSTRACT: C1 benzylated isoquinoline derivatives constitute the core of benzylisoquinoline alkaloids (BIAs). However, their C4 congeners remain elusive. Here, we describe a diastereoselective, catalytic, and modular C(sp³)-C(sp³) coupling protocol wherein β-amino sp³ C-H bonds of readily affordable vicinally functionalized dihydroisoquinolones are replaced by sp³ C-benzyl bonds. The method provides expedient access to C4 quaternary and homobenzylic dihydroisoquinolones, which are attractive fragments for potential drug discovery.

SUBMITTER: Beng TK 

PROVIDER: S-EPMC9050025 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature