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- Title
Reengineered BI-DIME Ligand Core Based on Computer Modeling to Increase Selectivity in Asymmetric Suzuki-Miyaura Coupling for the Challenging Axially Chiral HIV Integrase Inhibitor.
- Authors
Haddad, Nizar; Mangunuru, Hari P. R.; Fandrick, Keith R.; Qu, Bo; Sieber, Joshua D.; Rodriguez, Sonia; Desrosiers, Jean ‐ Nicolas; Patel, Nitinchandra D.; Lee, Heewon; Kurouski, Dmitry; Grinberg, Nelu; Yee, Nathan K.; Song, Jinhua J.; Senanayake, Chris H.
- Abstract
Through a computer-guided approach, new series of monophosphine ligands were designed and developed for asymmetric Suzuki-Miyaura couplings of challenging heterocyclic substrates. Computer modeling pointed to a tunable, yet unexplored quadrant in BI-DIME, leading to the discovery of the 3′,5′-dimethyl-substituted ligand which improved the atropisomeric selectivity of the Suzuki-Miyaura reaction from the previously reported 5:1 dr to 15:1 dr for the synthesis of a challenging HIV integrase intermediate, and up to 24:1 dr with various other quinoline substrates.
- Subjects
LIGANDS (Chemistry); HETEROCYCLIC compounds; SUZUKI reaction; COUPLING reactions (Chemistry); PALLADIUM catalysts
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 22, p3522
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600889