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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)orcid 
Publication Date: 2015
DOI: 10.1002/ejoc.201501083
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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
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
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