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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
- Source :
- Advanced Synthesis & Catalysis. 358:3522-3527
- Publication Year :
- 2016
- Publisher :
- Wiley, 2016.
-
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.
Details
- ISSN :
- 16154150
- Volume :
- 358
- Database :
- OpenAIRE
- Journal :
- Advanced Synthesis & Catalysis
- Accession number :
- edsair.doi...........d6e810be6ea7dfab71f5da954bd3c84a
- Full Text :
- https://doi.org/10.1002/adsc.201600889