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
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′‐dimeth...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2016-11, Vol.358 (22), p.3522-3527 |
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| container_title | Advanced synthesis & catalysis |
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| creator | 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. |
| description | 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. |
| doi_str_mv | 10.1002/adsc.201600889 |
| format | Article |
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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.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3979-6f53bbb1f8e3721daca89dd4353a186175475ec2ffb035d9d33b39e726af353b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>asymmetric Suzuki reaction</topic><topic>Asymmetry</topic><topic>atropisomers</topic><topic>BI-DIME</topic><topic>Computer simulation</topic><topic>Coupling</topic><topic>heterocycles</topic><topic>Ligands</topic><topic>Mathematical models</topic><topic>phosphine ligands</topic><topic>Selectivity</topic><topic>Substrates</topic><topic>Suzuki coupling</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Haddad, Nizar</creatorcontrib><creatorcontrib>Mangunuru, Hari P. 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| subjects | asymmetric Suzuki reaction Asymmetry atropisomers BI-DIME Computer simulation Coupling heterocycles Ligands Mathematical models phosphine ligands Selectivity Substrates Suzuki coupling Synthesis (chemistry) |
| 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 |
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