Palladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral y-Butyrolactones

Title
Palladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral y-Butyrolactones
Publication Date
2015
Author(s)
Stockton, Kieran
Merritt, Christopher
Sumby, Christopher J
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Wiley-VCH Verlag GmbH & Co KGaA
Place of publication
Germany
DOI
10.1002/ejoc.201501083
UNE publication id
une:18314
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.
Link
Citation
European Journal of Organic Chemistry, 2015(32), p. 6999-7008
ISSN
1099-0690
1434-193X
Start page
6999
End page
7008

Files:

NameSizeformatDescriptionLink