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

Authors

Timothy K. Beng, Central Washington University
Antonio Moreno, Central Washington University

Document Type

Article

Department or Administrative Unit

Chemistry

Publication Date

2-28-2020

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.

Comments

This article was originally published in RSC Advances. The full-text article from the publisher can be found here.

Recommended Citation

Beng, Timothy K. and Moreno, Antonio, "Catalytic, selective, and stereocontrolled construction of C4 quaternary and homobenzylic dihydroisoquinolones by sp3 C–H benzylation" (2020). All Faculty Scholarship for the College of the Sciences. 99.
https://digitalcommons.cwu.edu/cotsfac/99

Journal

RSC Advances

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License

Rights

© The Royal Society of Chemistry 2020