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https://hdl.handle.net/1959.11/18108
Title: | Palladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral y-Butyrolactones | Contributor(s): | Stockton, Kieran (author); Merritt, Christopher (author); Sumby, Christopher J (author); Greatrex, Ben (author)![]() |
Publication Date: | 2015 | DOI: | 10.1002/ejoc.201501083 | Handle Link: | https://hdl.handle.net/1959.11/18108 | Abstract: | The chiral pool material (-)-levoglucosenone (6,8-dioxabicyclo[3.2.1]oct-2-en-4-one, LGO) has been substituted by using a series of Pd-mediated cross-coupling reactions. Iodination of LGO followed by Suzuki-Miyaura cross-coupling reaction with boronic acids by employing the Buchwald ligand SPhos with Pd(OAc)₂ afforded 3-aryl derivatives in excellent yields. Selective Heck arylation reaction at the 2-position was achieved with aryl iodides with K₃PO₄ as base and SPhos ligand with Pd(OAc)₂ (1-5 mol-%). A selective hydroarylation reaction (formal conjugate addition) was developed by using the same aryl iodides, benzyldiethylamine, Pd-(OAc)₂, and P(o-tol)₃. The products were converted, either directly or after alkene reduction, through a Baeyer-Villiger oxidation into chiral 3- and 4-substituted 5-(hydroxymethyl)-dihydrofuran-2(3H)-ones. | Publication Type: | Journal Article | Source of Publication: | European Journal of Organic Chemistry, 2015(32), p. 6999-7008 | Publisher: | Wiley-VCH Verlag GmbH & Co KGaA | Place of Publication: | Germany | ISSN: | 1434-193X 1099-0690 |
Field of Research (FOR): | 030401 Biologically Active Molecules 030503 Organic Chemical Synthesis 030504 Organic Green Chemistry |
Socio-Economic Objective (SEO): | 970103 Expanding Knowledge in the Chemical Sciences 860899 Human Pharmaceutical Products not elsewhere classified |
Peer Reviewed: | Yes | HERDC Category Description: | C1 Refereed Article in a Scholarly Journal | Statistics to Oct 2018: | Visitors: 649 |
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Appears in Collections: | Journal Article |
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